You searched for subject:( cycloaddition).
Showing records 1 – 30 of
438 total matches.
◁ [1] [2] [3] [4] [5] … [15] ▶
Oregon State University
1.
Naffziger, Michael R.
Aryl acetylene substituent effects : the synthesis and application of biaryls.
Degree: MS, Chemistry, 2010, Oregon State University
URL: http://hdl.handle.net/1957/19650 
► The work described herein details the synthesis and application of biphenyls that probe the effects of hydrogen, Cl / Br, and methyl substituents on the…
(more)
▼ The work described herein details the synthesis and application of
biphenyls that probe the effects of hydrogen, Cl / Br, and methyl substituents
on the aryl ring of the terminal acetylenic carbon. From this work, we
successfully developed the rapid synthesis of phenyl acetylenes in 3-4 steps
from inexpensive commercially available materials. Using these mild
conditions, a wide host of functionalized acetylenes has been easily achieved,
avoiding complex and or difficult synthetic transformations
With the functionalized acetylenes in had, we demonstrated that the
subtle change from hydrogen to either methyl or halogen imparts diverse
results when subjected to [4+2] or [3+2] cycloadditions. This knowledge has
helped to explain other unexplained observations from previous work within
this project. These biphenyls were then further investigated by performing
various synthetically useful functional group transformations and comparing
the differences the substituents have on the corresponding reaction.
Noteworthy is the total synthesis of siamenol, a carbazole isolated from the
bark of Murriaya siamensis, where the key carbazole forming step is effected
by the substituents about the molecule in the synthesis of siamenol
derivatives.
Advisors/Committee Members: Carter, Richard G. (advisor), Kong, Wei (committee member).
Subjects/Keywords: cycloaddition
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Naffziger, M. R. (2010). Aryl acetylene substituent effects : the synthesis and application of biaryls. (Masters Thesis). Oregon State University. Retrieved from http://hdl.handle.net/1957/19650
Chicago Manual of Style (16th Edition):
Naffziger, Michael R. “Aryl acetylene substituent effects : the synthesis and application of biaryls.” 2010. Masters Thesis, Oregon State University. Accessed May 06, 2021.
http://hdl.handle.net/1957/19650.
MLA Handbook (7th Edition):
Naffziger, Michael R. “Aryl acetylene substituent effects : the synthesis and application of biaryls.” 2010. Web. 06 May 2021.
Vancouver:
Naffziger MR. Aryl acetylene substituent effects : the synthesis and application of biaryls. [Internet] [Masters thesis]. Oregon State University; 2010. [cited 2021 May 06].
Available from: http://hdl.handle.net/1957/19650.
Council of Science Editors:
Naffziger MR. Aryl acetylene substituent effects : the synthesis and application of biaryls. [Masters Thesis]. Oregon State University; 2010. Available from: http://hdl.handle.net/1957/19650
University of Alberta
2.
Chan, Bryan Chi Kit.
Cobalt(III)-Mediated Cycloalkenyl-Alkyne Cycloaddition and
Cycloexpansion Reactions.
Degree: PhD, Department of Chemistry, 2010, University of Alberta
URL: https://era.library.ualberta.ca/files/mw22v636t
► A comprehensive investigation of cycloalkenyl-alkyne coupling reactions mediated by cobalt(III) templates is presented. The in situ derived cationic η3-cyclohexenyl complexes of cobalt(III) react with some…
(more)
▼ A comprehensive investigation of cycloalkenyl-alkyne
coupling reactions mediated by cobalt(III) templates is presented.
The in situ derived cationic η3-cyclohexenyl complexes of
cobalt(III) react with some terminal alkynes to afford either
η1,η4-bicyclo[4.3.1]decadienyl or η2,η3-vinylcyclohexenyl products,
depending on the type and concentration of the alkyne. The
mechanism for this cyclohexenyl-alkyne cycloaddition reaction is
consistent with the previously reported cobalt-mediated [3 + 2 + 2]
allyl-alkyne coupling reaction. The carbon-carbon bond
activation/cyclopentenyl-alkyne ring expansion process was also
studied using the 1,3-di-tert-butylcyclopentadienyl cobalt system.
A modified synthetic strategy to the requisite half-sandwich
cobalt(I) cyclopentadiene precursor was developed using cobalt(II)
acetoacetonate, avoiding the use of simple cobalt(II) halides which
are prone to ligand disproportionation. Furthermore, the
preparation of the cobalt(III) cyclopentenyl precursor,
(t-Bu2C5H3)Co(η4-C5H6), was accomplished via hydride addition to
the easily prepared cobalticenium complex [(t-Bu2C5H3)Co(C5H5)]BF4
and avoids the use of the thermally sensitive
(t-Bu2C5H3)Co(ethylene)2. Disubstituted alkynes such as 2-butyne or
diphenylacetylene undergo cyclopentenyl coupling to afford the
corresponding η5-cycloheptadienyl products, albeit in lower yields
compared to the pentamethylcyclopentadienyl cobalt system. The
1,3-di-tert-butylcyclopentadienyl ancillary ligand shows unique and
unusual reactivity, coupling with tert-butylacetylene to afford a
novel spiro[4.5]decatrienyl complex. Ultimately, the poor isolated
yields of seven-membered products demonstrate that the
disubstituted cyclopentadienyl ligand system is a poor candidate
for future studies in this area. A mechanistic investigation of the
cobalt-mediated carbon-carbon bond activation process was
performed. Cationic cobalt η2-vinyl complexes were proposed as
viable intermediates in the activation process and synthetic routes
to these compounds were examined. However, the resulting vinyl
complexes were unstable and could not be directly isolated and
characterized. Preparation of cobalt vinyl complexes in the
presence of cycloalkadienes did not furnish the expected
cycloexpanded products, suggesting alternative routes to the cobalt
vinyl intermediates are necessary. During the course of the
mechanistic investigation, a high-yielding alternative synthetic
procedure for (C5Me5)Co(η4-butadiene) from the easily prepared
precursor, [(C5Me5)CoI2]n, was found, circumventing the use of the
thermally sensitive (C5Me5)Co(ethylene)2.
Subjects/Keywords: cycloexpansion; cycloalkenyl; cycloaddition
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Chan, B. C. K. (2010). Cobalt(III)-Mediated Cycloalkenyl-Alkyne Cycloaddition and
Cycloexpansion Reactions. (Doctoral Dissertation). University of Alberta. Retrieved from https://era.library.ualberta.ca/files/mw22v636t
Chicago Manual of Style (16th Edition):
Chan, Bryan Chi Kit. “Cobalt(III)-Mediated Cycloalkenyl-Alkyne Cycloaddition and
Cycloexpansion Reactions.” 2010. Doctoral Dissertation, University of Alberta. Accessed May 06, 2021.
https://era.library.ualberta.ca/files/mw22v636t.
MLA Handbook (7th Edition):
Chan, Bryan Chi Kit. “Cobalt(III)-Mediated Cycloalkenyl-Alkyne Cycloaddition and
Cycloexpansion Reactions.” 2010. Web. 06 May 2021.
Vancouver:
Chan BCK. Cobalt(III)-Mediated Cycloalkenyl-Alkyne Cycloaddition and
Cycloexpansion Reactions. [Internet] [Doctoral dissertation]. University of Alberta; 2010. [cited 2021 May 06].
Available from: https://era.library.ualberta.ca/files/mw22v636t.
Council of Science Editors:
Chan BCK. Cobalt(III)-Mediated Cycloalkenyl-Alkyne Cycloaddition and
Cycloexpansion Reactions. [Doctoral Dissertation]. University of Alberta; 2010. Available from: https://era.library.ualberta.ca/files/mw22v636t
NSYSU
3.
Huang, Chang-Gin.
An Efficient Synthesis of γ-Substituted α,β-Unsaturated δ-Lactams. Formal Synthesis of (±)-Protoemetinol.
Degree: Master, Chemistry, 2002, NSYSU
URL: http://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0618102-094444
γ-Substituted α,β-unsaturated δ-lactams was synthesized from α-sulfinyl acetamides in three steps.
Formal synthesis of (±)-Protoemetinol was also reported.
Advisors/Committee Members: Chou, C. H. (chair), Nein-Chen Chang (committee member), none (chair).Subjects/Keywords: cycloaddition reaction
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Huang, C. (2002). An Efficient Synthesis of γ-Substituted α,β-Unsaturated δ-Lactams. Formal Synthesis of (±)-Protoemetinol. (Thesis). NSYSU. Retrieved from http://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0618102-094444
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Huang, Chang-Gin. “An Efficient Synthesis of γ-Substituted α,β-Unsaturated δ-Lactams. Formal Synthesis of (±)-Protoemetinol.” 2002. Thesis, NSYSU. Accessed May 06, 2021.
http://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0618102-094444.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Huang, Chang-Gin. “An Efficient Synthesis of γ-Substituted α,β-Unsaturated δ-Lactams. Formal Synthesis of (±)-Protoemetinol.” 2002. Web. 06 May 2021.
Vancouver:
Huang C. An Efficient Synthesis of γ-Substituted α,β-Unsaturated δ-Lactams. Formal Synthesis of (±)-Protoemetinol. [Internet] [Thesis]. NSYSU; 2002. [cited 2021 May 06].
Available from: http://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0618102-094444.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Huang C. An Efficient Synthesis of γ-Substituted α,β-Unsaturated δ-Lactams. Formal Synthesis of (±)-Protoemetinol. [Thesis]. NSYSU; 2002. Available from: http://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0618102-094444
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Université du Québec à Montréal
4.
Zaghdane, Helmi.
Études synthétiques de la (-)-kopsine via un réarrangement d'Ireland-Claisen et une cycloaddition de Diels-Alder intramoléculaire.
Degree: 2008, Université du Québec à Montréal
URL: http://www.archipel.uqam.ca/1322/1/M10373.pdf
► La (-)-kopsine appartient à la famille des alcaloïdes aspidofractinine. Isolée pour la première fois en 1890 par l'équipe du professeur Ber à partir de plantes…
(more)
▼ La (-)-kopsine appartient à la famille des alcaloïdes aspidofractinine. Isolée pour la première fois en 1890 par l'équipe du professeur Ber à partir de plantes du genre Kopsia (Apocynaceae), qu'on retrouve abondamment dans le sud-est de l'Asie et qui sont connues dans la pharmacopée traditionnelle. En Chine, la Kopsia Officinalis est utilisée contre les douleurs rhumatismales tandis qu'en Malaisie, des plantes comme la Kopsia profunda, la Kopsia larutensis et la Kopsia teoi ont été utilisées comme antihypertenseurs, activité confirmée en laboratoire sur des rats normotendus. La synthèse de la kopsine et d'analogues s'avère donc intéressante au point de vue pharmacologique. Mais c'est au point de vue de la chimie que les défis sont à relever: la kopsine est une molécule complexe, qui comporte 7 cycles et 6 centres chiraux, dont 4 tétrasubstitués. La première synthèse énantiosélective de la (-)-kopsine qui vient d'être amorcée comporte une trentaine d'étapes. La première étape clé consiste en un réarrangement [3,3] d'Ireland-Claisen qui va permettre la formation du premier centre quaternaire de la molécule avec un transfert contrôlé de la chiralité en position 3 d'un dérivé oxindole. La deuxième étape clé consiste en une condensation d'iminiums en cascade, qui doit mener à la fomation de 2 cycles en une étape. Une troisième étape clé consiste en une réaction de cycloaddition de Diels-Alder intramoléculaire qui devra permettre de former les 2 derniers cycles de la (-)kopsine. Jusqu'à présent, deux volets de la synthèse ont été explorés. Dans un premier volet, l'iodooxindole a été couplé à un aldéhyde chiral dérivé de l'acide lactique par une condensation aldolique. La fonction alcool a été acylée avec différents chlorures d'acides et plusieurs conditions de réaction ont été essayées pour déclencher la première étape clé de la synthèse, soit le réarrangement [3,3]. Par ailleurs, l'application des conditions acides de Johnson a mis au jour une nouvelle réaction de cyclopropanation hautement stéréosélective. Dans un autre volet, la synthèse d'un substrat modèle a été amorcée pour éventuellement étudier la réaction de Diels-Alder et ainsi anticiper d'éventuels problèmes reliés à cette étape clé. La synthèse du composé modèle a débuté avec l'oxindole, qui a été allylé en position 3 puis alkylé avec le bromoacétate de méthyle. L'ester a été réduit, l'alcool obtenu a été protégé, le bromure d'allylmagnésium a été additionné sur le carbonyle du lactame et le diène résultant a été impliqué dans une réaction de cyclisation par métathèse d'alcène. Il reste quelques étapes à franchir, tel le couplage avec la contrepartie diénophile, pour que le composé tricyclique obtenu mène au substrat modèle de la cycloaddition de Diels-Alder intramoléculaire. ______________________________________________________________________________ MOTS-CLÉS DE L’AUTEUR : (-)-kopsine, Condensation aldolique, Cycloaddition de Diels-Alder Intramoléculaire, Réarrangement d'Ireland-Claisen, Oxindole, Condensation d'iminiums en cascade, Réaction de…
Subjects/Keywords: Alcaloïde; Cycloaddition; Kopsine; Synthèse chimique
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Zaghdane, H. (2008). Études synthétiques de la (-)-kopsine via un réarrangement d'Ireland-Claisen et une cycloaddition de Diels-Alder intramoléculaire. (Thesis). Université du Québec à Montréal. Retrieved from http://www.archipel.uqam.ca/1322/1/M10373.pdf
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Zaghdane, Helmi. “Études synthétiques de la (-)-kopsine via un réarrangement d'Ireland-Claisen et une cycloaddition de Diels-Alder intramoléculaire.” 2008. Thesis, Université du Québec à Montréal. Accessed May 06, 2021.
http://www.archipel.uqam.ca/1322/1/M10373.pdf.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Zaghdane, Helmi. “Études synthétiques de la (-)-kopsine via un réarrangement d'Ireland-Claisen et une cycloaddition de Diels-Alder intramoléculaire.” 2008. Web. 06 May 2021.
Vancouver:
Zaghdane H. Études synthétiques de la (-)-kopsine via un réarrangement d'Ireland-Claisen et une cycloaddition de Diels-Alder intramoléculaire. [Internet] [Thesis]. Université du Québec à Montréal; 2008. [cited 2021 May 06].
Available from: http://www.archipel.uqam.ca/1322/1/M10373.pdf.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Zaghdane H. Études synthétiques de la (-)-kopsine via un réarrangement d'Ireland-Claisen et une cycloaddition de Diels-Alder intramoléculaire. [Thesis]. Université du Québec à Montréal; 2008. Available from: http://www.archipel.uqam.ca/1322/1/M10373.pdf
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
5.
Santosh L Gaonkar.
Synthesis of biologically active heterocycles via
cycloaddition reactions; -.
Degree: Chemistry, 2006, University of Mysore
URL: http://shodhganga.inflibnet.ac.in/handle/10603/15929
► The thesis describes the synthesis of 1,2-oxazines, fused ring oxazines, newlinetetrahydropyridazines, fused ring pyridazines via [4+2] cycloaddition reactions newlinewhile 1,3,4-oxadiazoles, 2-isoxazolines, fused ring imidazoles etc…
(more)
▼ The thesis describes the synthesis of 1,2-oxazines,
fused ring oxazines, newlinetetrahydropyridazines, fused ring
pyridazines via [4+2] cycloaddition reactions newlinewhile
1,3,4-oxadiazoles, 2-isoxazolines, fused ring imidazoles etc via
1,3-dipolar newlinecycloaddition reactions employing new methods or
new reagents and results of newlineour study on the
functionalization of some 6-membered, 5-membered
newlineheterocycles and some of their biological activities. The
thesis describes new newlinemethod for the generation of
and#945;-nitrosoolefins from ketooximes, azoalkenes from
newlineketohydrazones using chloramine-T as new reagent and their
applications in the newlinesynthesis of 1,2-oxazines and
tetrahydropyridazines respectively via [4+2] newlinecycloaddition
reactions. A new series 2-{4-[2-(5-ethylpyridin-2-
newlineyl)ethoxy]phenyl}-5-substituted-1,3,4-oxadiazoles are
synthesized via 1,3-dipolar newlinecycloaddition reactions and
evaluated for antimicrobial and anticancer activities. newlineA new
series of 3-[5-ethyl-2-(2-phenoxy-ethyl)-pyridin]-5-substituted
newlineisoxazolines are synthesized via intermolecular 1,3- dipolar
cycloaddition newlinereactions and evaluated for antimicrobial
activity. The thesis also describes newlineapplications
2-butyl-5-chloro-3H-imidazole-4-carbaldehyde in the synthesis of
newlinefused ring isoxazolines and pyrazolines via intramolecular
1,3-dipolar newlinecycloaddition reactions.
References given chapter wise
Advisors/Committee Members: Loknath Rai.
Subjects/Keywords: Chemistry; cycloaddition reactions; heterocycles
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Gaonkar, S. L. (2006). Synthesis of biologically active heterocycles via
cycloaddition reactions; -. (Thesis). University of Mysore. Retrieved from http://shodhganga.inflibnet.ac.in/handle/10603/15929
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Gaonkar, Santosh L. “Synthesis of biologically active heterocycles via
cycloaddition reactions; -.” 2006. Thesis, University of Mysore. Accessed May 06, 2021.
http://shodhganga.inflibnet.ac.in/handle/10603/15929.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Gaonkar, Santosh L. “Synthesis of biologically active heterocycles via
cycloaddition reactions; -.” 2006. Web. 06 May 2021.
Vancouver:
Gaonkar SL. Synthesis of biologically active heterocycles via
cycloaddition reactions; -. [Internet] [Thesis]. University of Mysore; 2006. [cited 2021 May 06].
Available from: http://shodhganga.inflibnet.ac.in/handle/10603/15929.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Gaonkar SL. Synthesis of biologically active heterocycles via
cycloaddition reactions; -. [Thesis]. University of Mysore; 2006. Available from: http://shodhganga.inflibnet.ac.in/handle/10603/15929
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
6.
Wagner, Bernd.
Homogene Goldkatalyse zur Darstellung neuartiger heterocyclischer Spiroverbindungen.
Degree: 2016, Technische Universität Dortmund
URL: http://dx.doi.org/10.17877/DE290R-17255
► In recent years, a variety of new entries to interesting heterocylic compounds has been reported in the field of gold catalysis. On this occasion, it…
(more)
▼ In recent years, a variety of new entries to interesting heterocylic compounds has been reported in the field of gold catalysis. On this occasion, it is possible to form new C-O, C-N, C-S or C-C bonds under usually mild reaction conditions. This work generally deals with new gold catalyzed methodologies for the synthesis of heterocyclic spiro compounds. On the one hand, it was possible to develop an entry to spirocyclic pyrazolidines via a multicomponent approach with an alkynol, a hydrazine and a carbonyl compound. In the process, four new bonds are formed with just releasing water as a by-product. Furthermore, this highly atom economic reaction is practicable in aqueous systems. For the first time corresponding DNA-conjugates could be synthesized with this methodology. This discloses a new synthetic tool in the research field of medicinal chemistry for the construction of DNA-encoded compound libraries. Also In further studies gold catalyzed
syntheses of spirocyclic isoxazolidines and α,β-unsaturated lactones were carried out. In these cases the aspect should be economic synthesis routes as well.
Advisors/Committee Members: Krause, Norbert (advisor), Hiersemann, Martin (referee).
Subjects/Keywords: Goldkatalyse; Spiroacetale; Alkine; Cycloaddition; 540
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Wagner, B. (2016). Homogene Goldkatalyse zur Darstellung neuartiger heterocyclischer Spiroverbindungen. (Doctoral Dissertation). Technische Universität Dortmund. Retrieved from http://dx.doi.org/10.17877/DE290R-17255
Chicago Manual of Style (16th Edition):
Wagner, Bernd. “Homogene Goldkatalyse zur Darstellung neuartiger heterocyclischer Spiroverbindungen.” 2016. Doctoral Dissertation, Technische Universität Dortmund. Accessed May 06, 2021.
http://dx.doi.org/10.17877/DE290R-17255.
MLA Handbook (7th Edition):
Wagner, Bernd. “Homogene Goldkatalyse zur Darstellung neuartiger heterocyclischer Spiroverbindungen.” 2016. Web. 06 May 2021.
Vancouver:
Wagner B. Homogene Goldkatalyse zur Darstellung neuartiger heterocyclischer Spiroverbindungen. [Internet] [Doctoral dissertation]. Technische Universität Dortmund; 2016. [cited 2021 May 06].
Available from: http://dx.doi.org/10.17877/DE290R-17255.
Council of Science Editors:
Wagner B. Homogene Goldkatalyse zur Darstellung neuartiger heterocyclischer Spiroverbindungen. [Doctoral Dissertation]. Technische Universität Dortmund; 2016. Available from: http://dx.doi.org/10.17877/DE290R-17255
University of Guelph
7.
Haner, Jamie.
Synthesis of Substituted Oxabenzonorbornadienes and their Reactions.
Degree: MS, Department of Chemistry, 2011, University of Guelph
URL: https://atrium.lib.uoguelph.ca/xmlui/handle/10214/2958
► This thesis describes investigations on the topic of the versatile organic scaffold, 7-oxabenzonorbornadiene. The synthesis of 2-alkyl substituted furans via iron-catalyzed coupling of Grignard reagents…
(more)
▼ This thesis describes investigations on the topic of the versatile organic scaffold, 7-oxabenzonorbornadiene. The synthesis of 2-alkyl substituted furans via iron-catalyzed coupling of Grignard reagents and 2-bromofuran was optimized and various groups were coupled to furan. Primary and secondary alkyl groups were coupled with moderate to low yields of up to 56% were obtained. Furan-benzyne
cycloaddition led to the formation of the corresponding C-1 substituted oxabenzonorbornadiene in yields of up to 70%. This methodology allows for access to uniquely substituted, strained bicyclic alkenes for further studies. The second part of this thesis describes the cyclopropanation of oxabenzonorbornadiene and the subsequent discovery of several reactions of the cyclopropane. The conditions for cyclopropanation were optimized, obtaining this product in yields of up to 98%. Treatment of this cyclopropane under electrophilic conditions led to the formation of (2-naphthyl)methanes in up to 98% yields, whereas treatment under nucleophilic conditions led to the formation of dihydronaphthols in up to >99% yield. The optimization of these reactions and mechanistic studies are described.
Advisors/Committee Members: Tam, William (advisor).
Subjects/Keywords: Oxabenzonorbornadiene; Cycloaddition; Organic Chemistry; Synthesis
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Haner, J. (2011). Synthesis of Substituted Oxabenzonorbornadienes and their Reactions. (Masters Thesis). University of Guelph. Retrieved from https://atrium.lib.uoguelph.ca/xmlui/handle/10214/2958
Chicago Manual of Style (16th Edition):
Haner, Jamie. “Synthesis of Substituted Oxabenzonorbornadienes and their Reactions.” 2011. Masters Thesis, University of Guelph. Accessed May 06, 2021.
https://atrium.lib.uoguelph.ca/xmlui/handle/10214/2958.
MLA Handbook (7th Edition):
Haner, Jamie. “Synthesis of Substituted Oxabenzonorbornadienes and their Reactions.” 2011. Web. 06 May 2021.
Vancouver:
Haner J. Synthesis of Substituted Oxabenzonorbornadienes and their Reactions. [Internet] [Masters thesis]. University of Guelph; 2011. [cited 2021 May 06].
Available from: https://atrium.lib.uoguelph.ca/xmlui/handle/10214/2958.
Council of Science Editors:
Haner J. Synthesis of Substituted Oxabenzonorbornadienes and their Reactions. [Masters Thesis]. University of Guelph; 2011. Available from: https://atrium.lib.uoguelph.ca/xmlui/handle/10214/2958
8.
Rajotte, Isabelle.
Efforts vers la synthèse totale de la cylindrocarine par
cycloaddition intramoléculaire impliquant des aminocarbènes de
chrome.
Degree: M. Sc., Chimie, 2016, Université de Sherbrooke
URL: http://www.collectionscanada.gc.ca/obj/thesescanada/vol2/QSHERU/TC-QSHERU-11143_8742.pdf
;
http://savoirs.usherbrooke.ca/bitstream/11143/8742/3/Rajotte_Isabelle_MSc_2016.pdf
► Des travaux précédents ont explorés la réactivité des aminocarbènes de chrome. Dans cet ouvrage, il sera question d’appliquer cette réactivité à la synthèse de la…
(more)
▼ Des travaux précédents ont explorés la réactivité des
aminocarbènes de chrome. Dans cet ouvrage, il sera question
d’appliquer cette réactivité à la synthèse de la cylindrocarine qui
est de la famille des alcaloïdes indoliques, les aspidosperma.
Le premier chapitre traitera de la réaction entre un aminocarbène
de chrome et un diène dans le but de former une diénamine. Il sera
question de la réactivité entre les aminocarbènes de chrome et les
diènes sur un substrat portant un groupement indole. Aussi, il y
est expliqué pourquoi le manque de réactivité entre les diénamines
et les indoles nous a poussés à se tourner vers une nouvelle
approche de synthèse.
Le deuxième chapitre présente des
métathèses entre des aminocarbènes de chrome et des fonctions
alcynes dans le but de former des aminocarbènes de chrome
vinylogues. Il sera question de la stabilité des aminocarbènes de
chrome vinylogues et de la possibilité de les piéger de manière
intra- et intermoléculaire. Aussi, la portée de cette réaction sera
déterminée en étudiant l’influence de différents groupements
fonctionnels sur l’alcyne.
Dans le troisième chapitre, il sera
question de la réaction entre un aminocarbène de chrome de type
lactame et de sa réactivité vis-à-vis une double liaison
intramoléculaire pour permettre la formation d’un composé
bicyclique. La portée de cette réaction sera étudiée en ajoutant
des groupements fonctionnels à différents endroits sur la
molécule.
Advisors/Committee Members: Spino, Claude.
Subjects/Keywords: Cylindrocarine; Aminocarbène; Cycloaddition; Chrome; Aspidosperma
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Rajotte, I. (2016). Efforts vers la synthèse totale de la cylindrocarine par
cycloaddition intramoléculaire impliquant des aminocarbènes de
chrome. (Masters Thesis). Université de Sherbrooke. Retrieved from http://www.collectionscanada.gc.ca/obj/thesescanada/vol2/QSHERU/TC-QSHERU-11143_8742.pdf ; http://savoirs.usherbrooke.ca/bitstream/11143/8742/3/Rajotte_Isabelle_MSc_2016.pdf
Chicago Manual of Style (16th Edition):
Rajotte, Isabelle. “Efforts vers la synthèse totale de la cylindrocarine par
cycloaddition intramoléculaire impliquant des aminocarbènes de
chrome.” 2016. Masters Thesis, Université de Sherbrooke. Accessed May 06, 2021.
http://www.collectionscanada.gc.ca/obj/thesescanada/vol2/QSHERU/TC-QSHERU-11143_8742.pdf ; http://savoirs.usherbrooke.ca/bitstream/11143/8742/3/Rajotte_Isabelle_MSc_2016.pdf.
MLA Handbook (7th Edition):
Rajotte, Isabelle. “Efforts vers la synthèse totale de la cylindrocarine par
cycloaddition intramoléculaire impliquant des aminocarbènes de
chrome.” 2016. Web. 06 May 2021.
Vancouver:
Rajotte I. Efforts vers la synthèse totale de la cylindrocarine par
cycloaddition intramoléculaire impliquant des aminocarbènes de
chrome. [Internet] [Masters thesis]. Université de Sherbrooke; 2016. [cited 2021 May 06].
Available from: http://www.collectionscanada.gc.ca/obj/thesescanada/vol2/QSHERU/TC-QSHERU-11143_8742.pdf ; http://savoirs.usherbrooke.ca/bitstream/11143/8742/3/Rajotte_Isabelle_MSc_2016.pdf.
Council of Science Editors:
Rajotte I. Efforts vers la synthèse totale de la cylindrocarine par
cycloaddition intramoléculaire impliquant des aminocarbènes de
chrome. [Masters Thesis]. Université de Sherbrooke; 2016. Available from: http://www.collectionscanada.gc.ca/obj/thesescanada/vol2/QSHERU/TC-QSHERU-11143_8742.pdf ; http://savoirs.usherbrooke.ca/bitstream/11143/8742/3/Rajotte_Isabelle_MSc_2016.pdf
University of Ottawa
9.
Ranasinghe Gamage, Indeewari.
New Reactivity Involving N-Isothiocyanates: Aminothiocarbonylation and [3+2] Cycloadditions to Form Molecules Containing NNCS Motifs
.
Degree: 2017, University of Ottawa
URL: http://hdl.handle.net/10393/36042
► Nitrogen-containing heterocycles are of vital importance for the pharmaceutical and agrochemical industries. The Beauchemin group has been studying rare, amphoteric nitrogen-substituted isocyanates over the past…
(more)
▼ Nitrogen-containing heterocycles are of vital importance for the pharmaceutical and agrochemical industries. The Beauchemin group has been studying rare, amphoteric nitrogen-substituted isocyanates over the past years, and showed that their [3+2] alkene cycloaddition and cascade reactions provide access to a variety of NNCO containing heterocyclic compounds. This triggered interest into the reactivity of the parent N-isothiocyanates, which are also rare, and led to the discovery of aminothiocarbonylation reactions. The products formed are azomethine imines which contain a cyclic -aminothiocarbonyl motif, thus providing a cycloaddition route to these useful dipoles from simple starting materials. Such aminothiocarbonylation reactions were developed with both alkenes and imines as substrates.Apart from cyclic azomethine imine formations, efforts have also been made toward forming the acyclic azomethine imines as intermediates. These intermediates undergo [3+2] cycloaddition to form thiocarbamoyl pyrazolidine derivatives, and a preliminary substrate scope for this new intermolecular reactivity is presented. Other preliminary results include an unexpected Chugaev type reactivity. Collectively, these results show that N-isothiocyanates hold significant potential for the development of new reactivity.
Subjects/Keywords: aminothiocarbonylation;
heterocycles;
cycloaddition;
isothiocyanates
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Ranasinghe Gamage, I. (2017). New Reactivity Involving N-Isothiocyanates: Aminothiocarbonylation and [3+2] Cycloadditions to Form Molecules Containing NNCS Motifs
. (Thesis). University of Ottawa. Retrieved from http://hdl.handle.net/10393/36042
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Ranasinghe Gamage, Indeewari. “New Reactivity Involving N-Isothiocyanates: Aminothiocarbonylation and [3+2] Cycloadditions to Form Molecules Containing NNCS Motifs
.” 2017. Thesis, University of Ottawa. Accessed May 06, 2021.
http://hdl.handle.net/10393/36042.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Ranasinghe Gamage, Indeewari. “New Reactivity Involving N-Isothiocyanates: Aminothiocarbonylation and [3+2] Cycloadditions to Form Molecules Containing NNCS Motifs
.” 2017. Web. 06 May 2021.
Vancouver:
Ranasinghe Gamage I. New Reactivity Involving N-Isothiocyanates: Aminothiocarbonylation and [3+2] Cycloadditions to Form Molecules Containing NNCS Motifs
. [Internet] [Thesis]. University of Ottawa; 2017. [cited 2021 May 06].
Available from: http://hdl.handle.net/10393/36042.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Ranasinghe Gamage I. New Reactivity Involving N-Isothiocyanates: Aminothiocarbonylation and [3+2] Cycloadditions to Form Molecules Containing NNCS Motifs
. [Thesis]. University of Ottawa; 2017. Available from: http://hdl.handle.net/10393/36042
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Université de Sherbrooke
10.
Rajotte, Isabelle.
Efforts vers la synthèse totale de la cylindrocarine par cycloaddition intramoléculaire impliquant des aminocarbènes de chrome.
Degree: 2016, Université de Sherbrooke
URL: http://hdl.handle.net/11143/8742
► Des travaux précédents ont explorés la réactivité des aminocarbènes de chrome. Dans cet ouvrage, il sera question d’appliquer cette réactivité à la synthèse de la…
(more)
▼ Des travaux précédents ont explorés la réactivité des aminocarbènes de chrome. Dans cet ouvrage, il sera question d’appliquer cette réactivité à la synthèse de la cylindrocarine qui est de la famille des alcaloïdes indoliques, les aspidosperma.
Le premier chapitre traitera de la réaction entre un aminocarbène de chrome et un diène dans le but de former une diénamine. Il sera question de la réactivité entre les aminocarbènes de chrome et les diènes sur un substrat portant un groupement indole. Aussi, il y est expliqué pourquoi le manque de réactivité entre les diénamines et les indoles nous a poussés à se tourner vers une nouvelle approche de synthèse.
Le deuxième chapitre présente des métathèses entre des aminocarbènes de chrome et des fonctions alcynes dans le but de former des aminocarbènes de chrome vinylogues. Il sera question de la stabilité des aminocarbènes de chrome vinylogues et de la possibilité de les piéger de manière intra- et intermoléculaire. Aussi, la portée de cette réaction sera déterminée en étudiant l’influence de différents groupements fonctionnels sur l’alcyne.
Dans le troisième chapitre, il sera question de la réaction entre un aminocarbène de chrome de type lactame et de sa réactivité vis-à-vis une double liaison intramoléculaire pour permettre la formation d’un composé bicyclique. La portée de cette réaction sera étudiée en ajoutant des groupements fonctionnels à différents endroits sur la molécule.
Advisors/Committee Members: Spino, Claude (advisor).
Subjects/Keywords: Cylindrocarine; Aminocarbène; Cycloaddition; Chrome; Aspidosperma
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Rajotte, I. (2016). Efforts vers la synthèse totale de la cylindrocarine par cycloaddition intramoléculaire impliquant des aminocarbènes de chrome. (Masters Thesis). Université de Sherbrooke. Retrieved from http://hdl.handle.net/11143/8742
Chicago Manual of Style (16th Edition):
Rajotte, Isabelle. “Efforts vers la synthèse totale de la cylindrocarine par cycloaddition intramoléculaire impliquant des aminocarbènes de chrome.” 2016. Masters Thesis, Université de Sherbrooke. Accessed May 06, 2021.
http://hdl.handle.net/11143/8742.
MLA Handbook (7th Edition):
Rajotte, Isabelle. “Efforts vers la synthèse totale de la cylindrocarine par cycloaddition intramoléculaire impliquant des aminocarbènes de chrome.” 2016. Web. 06 May 2021.
Vancouver:
Rajotte I. Efforts vers la synthèse totale de la cylindrocarine par cycloaddition intramoléculaire impliquant des aminocarbènes de chrome. [Internet] [Masters thesis]. Université de Sherbrooke; 2016. [cited 2021 May 06].
Available from: http://hdl.handle.net/11143/8742.
Council of Science Editors:
Rajotte I. Efforts vers la synthèse totale de la cylindrocarine par cycloaddition intramoléculaire impliquant des aminocarbènes de chrome. [Masters Thesis]. Université de Sherbrooke; 2016. Available from: http://hdl.handle.net/11143/8742
11.
LOCKETT-WALTERS, BRUCE.
The Tamura Cycloaddition: Mechanism and Enantiocontrol.
Degree: School of Chemistry. Discipline of Chemistry, 2019, Trinity College Dublin
URL: http://hdl.handle.net/2262/88750
► This thesis documents attempts to employ succinimide derivatives as ?anhydride surrogates? in the organocatalytic cycloaddition between aryl succinic anhydrides and various electrophiles previously developed in…
(more)
▼ This thesis documents attempts to employ succinimide derivatives as ?anhydride surrogates? in the organocatalytic
cycloaddition between aryl succinic anhydrides and various electrophiles previously developed in our research group. Although such a process remains elusive, valuable insight into the required substrate reactivity has been gained.
Thirty-eight years on from the original publication of the Tamura
cycloaddition between homophthalic anhydride and activated alkenes/alkynes, a combined experimental and computational investigation has revealed the base-catalysed reaction previously thought of as a Diels-Alder type process proceeds via a stepwise mechanism involving conjugate addition and ring closure ? verified by both DFT calculations and the isolation of an intermediate Michael-type adduct which represents the first example of a catalytic ?- substitution reaction of anhydrides. The calculated reaction pathway was validated through the experimental confirmation of a theoretical prediction that a cyclisation step resistant to catalysis by Hu?nig?s base could smoothly occur in the presence of a smaller amine. Succinic anhydrides are also compatible with the process and react with maleimides to afford chiral ?-substituted anhydride addition products of considerable synthetic potential. Cinchona alkaloid derived organocatalysts were later found to promote this reaction enantioselectively. The Michael adduct formed could be derivatised via aminolysis of the anhydride moiety at low temperature, which allowed the formation of a bis-imide structure bearing two contiguous stereocentres (one all carbon quaternary) in near optical purity. The scope of the reaction with respect to the anhydride component was later extended; however only aryl succinic anhydrides substituted with highly electron withdrawing groups were found to react at a practical rate.
A number of substituted aryl succinic anhydrides synthesised for extension of the scope of the catalytic ?-substitution were fortuitously employed in an asymmetric organocatalytic
cycloaddition with imines to afford substituted ?-lactams in high levels of optical purity.
Advisors/Committee Members: Connon, Stephen.
Subjects/Keywords: Succinimide derivatives; Tamura cycloaddition
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
LOCKETT-WALTERS, B. (2019). The Tamura Cycloaddition: Mechanism and Enantiocontrol. (Thesis). Trinity College Dublin. Retrieved from http://hdl.handle.net/2262/88750
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
LOCKETT-WALTERS, BRUCE. “The Tamura Cycloaddition: Mechanism and Enantiocontrol.” 2019. Thesis, Trinity College Dublin. Accessed May 06, 2021.
http://hdl.handle.net/2262/88750.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
LOCKETT-WALTERS, BRUCE. “The Tamura Cycloaddition: Mechanism and Enantiocontrol.” 2019. Web. 06 May 2021.
Vancouver:
LOCKETT-WALTERS B. The Tamura Cycloaddition: Mechanism and Enantiocontrol. [Internet] [Thesis]. Trinity College Dublin; 2019. [cited 2021 May 06].
Available from: http://hdl.handle.net/2262/88750.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
LOCKETT-WALTERS B. The Tamura Cycloaddition: Mechanism and Enantiocontrol. [Thesis]. Trinity College Dublin; 2019. Available from: http://hdl.handle.net/2262/88750
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
University of Minnesota
12.
Jarvi, Melissa.
Regioselective Synthesis of Isoxazoles by Hypervalent Iodine(III) Reagent Mediated Oxidative Cycloaddition.
Degree: MS, Chemistry, 2019, University of Minnesota
URL: http://hdl.handle.net/11299/208932
► Isoxazole is a five membered heterocyclic compound containing oxygen and nitrogen atoms in the 1,2 positions. Isoxazole rings are found in natural products, such as…
(more)
▼ Isoxazole is a five membered heterocyclic compound containing oxygen and nitrogen atoms in the 1,2 positions. Isoxazole rings are found in natural products, such as ibotenic acid and muscimol. The isoxazole structure is incorporated in a variety of pharmaceutical agents. Substitution on different positions on the nucleus of the isoxazole results in various pharmacological effects. Specifically, isoxazole compounds are used in various types of pharmaceutical compounds to treat bacterial infections and pain relief. Oxidative cycloaddition of aldoximes with unsaturated substrates provides an efficient approach to the formation of heterocyclic compounds. More specifically, various isoxazoles can be easily prepared by the oxidative cycloaddition of aldoximes with unsaturated substrates in the presence of hypervalent iodine(III) reagents. Oxidation of aldoximes by hypervalent iodine(III) compounds produces nitrile oxides which further react with respective unsaturated substrates through a 1,3-dipolar cycloaddition reaction resulting in various isoxazole products. This technique is an efficient process that utilizes green chemistry. Here, we report an efficient synthetic approach for preparation of various regioselective 3,4-substituted isoxazoles and 3,4,5-substituted isoxazoles using [hydroxy(tosyloxy)iodo]benzene, commonly known as Koser’s reagent. To our knowledge, this is the first time the 3,4-substituted isoxazole has been prepared. The oxidative cycloaddition proceeds at room temperature resulting in moderate to high yields. Structures of several isoxazole derivatives were established by X-ray crystallography. These isoxazole derivatives are stable compounds that have the potential to be useful for biologically active molecules and pharmaceutical reagents.
Subjects/Keywords: Cycloaddition; Hypervalent iodine(III); Isoxazole
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Jarvi, M. (2019). Regioselective Synthesis of Isoxazoles by Hypervalent Iodine(III) Reagent Mediated Oxidative Cycloaddition. (Masters Thesis). University of Minnesota. Retrieved from http://hdl.handle.net/11299/208932
Chicago Manual of Style (16th Edition):
Jarvi, Melissa. “Regioselective Synthesis of Isoxazoles by Hypervalent Iodine(III) Reagent Mediated Oxidative Cycloaddition.” 2019. Masters Thesis, University of Minnesota. Accessed May 06, 2021.
http://hdl.handle.net/11299/208932.
MLA Handbook (7th Edition):
Jarvi, Melissa. “Regioselective Synthesis of Isoxazoles by Hypervalent Iodine(III) Reagent Mediated Oxidative Cycloaddition.” 2019. Web. 06 May 2021.
Vancouver:
Jarvi M. Regioselective Synthesis of Isoxazoles by Hypervalent Iodine(III) Reagent Mediated Oxidative Cycloaddition. [Internet] [Masters thesis]. University of Minnesota; 2019. [cited 2021 May 06].
Available from: http://hdl.handle.net/11299/208932.
Council of Science Editors:
Jarvi M. Regioselective Synthesis of Isoxazoles by Hypervalent Iodine(III) Reagent Mediated Oxidative Cycloaddition. [Masters Thesis]. University of Minnesota; 2019. Available from: http://hdl.handle.net/11299/208932
13.
Tsetan, Kunga.
JULIA-KOCIENSKI APPROACH TO 4-SUBSTITUTED 1- ALKENYL-1H-1,2,3-TRIAZOLES.
Degree: MS(M.S.), Chemistry, 2016, City University of New York
URL: https://academicworks.cuny.edu/cc_etds_theses/610
► A modular approach to the synthesis of 4-substituted N-vinyltriazoles was developed. The triazole cores were assembled by copper-catalyzed 1,3-dipolar cycloaddition of 1-phenyl-1H-tetrazol-5-yl (PT) azidomethyl…
(more)
▼ A modular approach to the synthesis of 4-substituted N-vinyltriazoles was developed. The triazole cores were assembled by copper-catalyzed 1,3-dipolar
cycloaddition of 1-phenyl-1H-tetrazol-5-yl (PT) azidomethyl sulfide with: pmethoxyphenyl, 2-pyridyl, and triisopropylsilyl alkynes. Subsequent oxidation of the sulfides furnished 4-substituted triazoles with a Julia-Kocienski olefination handle attached at the N1 atom of the triazole. Olefination reactions of triazole-derived Julia-Kocienski reagents with paraformaldehyde gave 1-ethenyl-1H-1,2,3-triazoles. Heck reactions of these products with phenyl or p-methoxyphenyl iodide led to further functionalization of the terminal carbon, with E/Z-olefin ratios ≥ 92%. Heck reaction with p-cyanophenyl iodide gave low conversion, and that with 2-thienyl iodide did not proceed. On the other hand, Julia-Kocienski olefinations proceeded with electron-rich and electron-deficient aryl, as well as alkyl aldehydes. The resulting 1,2-disubstituted alkenes were formed in good yields, but with moderate to poor E/Z-selectivities. A modular approach to the synthesis of 4-substituted N-vinyltriazoles was developed. The triazole cores were assembled by copper-catalyzed 1,3-dipolar
cycloaddition of 1-phenyl-1H-tetrazol-5-yl (PT) azidomethyl sulfide with: pmethoxyphenyl, 2-pyridyl, and triisopropylsilyl alkynes. Subsequent oxidation of the sulfides furnished 4-substituted triazoles with a Julia-Kocienski olefination handle attached at the N1 atom of the triazole. Olefination reactions of triazole-derived Julia-Kocienski reagents with paraformaldehyde gave 1-ethenyl-1H-1,2,3-triazoles. Heck reactions of these products with phenyl or p-methoxyphenyl iodide led to further functionalization of the terminal carbon, with E/Z-olefin ratios ≥ 92%. Heck reaction with p-cyanophenyl iodide gave low conversion, and that with 2-thienyl iodide did not proceed. On the other hand, Julia-Kocienski olefinations proceeded with electron-rich and electron-deficient aryl, as well as alkyl aldehydes. The resulting 1,2-disubstituted alkenes were formed in good yields, but with moderate to poor E/Z-selectivities.
Advisors/Committee Members: Barbara Zajc, Mahesh Lakshman, Urs Jans.
Subjects/Keywords: triazole; cycloaddition; olefination; Chemistry
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Tsetan, K. (2016). JULIA-KOCIENSKI APPROACH TO 4-SUBSTITUTED 1- ALKENYL-1H-1,2,3-TRIAZOLES. (Thesis). City University of New York. Retrieved from https://academicworks.cuny.edu/cc_etds_theses/610
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Tsetan, Kunga. “JULIA-KOCIENSKI APPROACH TO 4-SUBSTITUTED 1- ALKENYL-1H-1,2,3-TRIAZOLES.” 2016. Thesis, City University of New York. Accessed May 06, 2021.
https://academicworks.cuny.edu/cc_etds_theses/610.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Tsetan, Kunga. “JULIA-KOCIENSKI APPROACH TO 4-SUBSTITUTED 1- ALKENYL-1H-1,2,3-TRIAZOLES.” 2016. Web. 06 May 2021.
Vancouver:
Tsetan K. JULIA-KOCIENSKI APPROACH TO 4-SUBSTITUTED 1- ALKENYL-1H-1,2,3-TRIAZOLES. [Internet] [Thesis]. City University of New York; 2016. [cited 2021 May 06].
Available from: https://academicworks.cuny.edu/cc_etds_theses/610.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Tsetan K. JULIA-KOCIENSKI APPROACH TO 4-SUBSTITUTED 1- ALKENYL-1H-1,2,3-TRIAZOLES. [Thesis]. City University of New York; 2016. Available from: https://academicworks.cuny.edu/cc_etds_theses/610
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Brock University
14.
Bissett, Tyler.
Explorations of Intramolecular [5+2] Cycloadditions of Ring-Constrained Vinylcyclopropanes
.
Degree: Department of Chemistry, 2014, Brock University
URL: http://hdl.handle.net/10464/5741
► The first example of a [5+2] cycloaddition reaction wherein the olefin of the vinylcyclopropyl moiety is constrained in a carbocycle was explored, and possible reasons…
(more)
▼ The first example of a [5+2] cycloaddition reaction wherein the olefin of the
vinylcyclopropyl moiety is constrained in a carbocycle was explored, and possible reasons on the lack of reactivity of the substrate were studied. A simple model substrate was synthesized and subjected to cycloaddition conditions to determine if the reason for the lack of reactivity was related to the complexity of the substrate, or if the lack of “conjugative character” of the cyclopropyl ring with respect to the olefin is responsible. A more complex bicyclic substrate possessing an angular methyl group at the ring junction was also synthesized and explored, with evidence supporting the current theory of deconjugation of the cyclopropyl moiety.
Subjects/Keywords: cycloaddition reaction;
vinylcyclopropyl moiety
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Bissett, T. (2014). Explorations of Intramolecular [5+2] Cycloadditions of Ring-Constrained Vinylcyclopropanes
. (Thesis). Brock University. Retrieved from http://hdl.handle.net/10464/5741
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Bissett, Tyler. “Explorations of Intramolecular [5+2] Cycloadditions of Ring-Constrained Vinylcyclopropanes
.” 2014. Thesis, Brock University. Accessed May 06, 2021.
http://hdl.handle.net/10464/5741.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Bissett, Tyler. “Explorations of Intramolecular [5+2] Cycloadditions of Ring-Constrained Vinylcyclopropanes
.” 2014. Web. 06 May 2021.
Vancouver:
Bissett T. Explorations of Intramolecular [5+2] Cycloadditions of Ring-Constrained Vinylcyclopropanes
. [Internet] [Thesis]. Brock University; 2014. [cited 2021 May 06].
Available from: http://hdl.handle.net/10464/5741.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Bissett T. Explorations of Intramolecular [5+2] Cycloadditions of Ring-Constrained Vinylcyclopropanes
. [Thesis]. Brock University; 2014. Available from: http://hdl.handle.net/10464/5741
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Université de Sherbrooke
15.
D. Lefebvre, Louis-Philippe.
Développement d'une réaction de cycloaddition (4+1) intramoléculaire formelle impliquant des aminocarbènes de chrome.
Degree: 2012, Université de Sherbrooke
URL: http://hdl.handle.net/11143/5752
► Ce mémoire résume les percées effectuées vers le développement d'une réaction de cycloaddition (4+1) intramoléculaire formelle entre des aminocarbènes de chrome et des diènes. Une…
(more)
▼ Ce mémoire résume les percées effectuées vers le développement d'une réaction de
cycloaddition (4+1) intramoléculaire formelle entre des aminocarbènes de chrome et des diènes. Une telle réaction n'est pas connue dans la littérature et permettrait de fabriquer des bicycles présentant un cyclopentène, structure intéressante et levier synthétique puissant en synthèse organique. Dans le premier chapitre, on retrouve les essais initiaux concernant des réactions intermoléculaires entre des diènes pauvres en électrons et différents carbènes de chrome. Il y est expliqué pourquoi les résultats mitigés obtenus nous ont poussés à nous tourner vers une approche intramoléculaire de la méthodologie. Le second chapitre présente les premiers résultats de
cycloaddition (4+1) intramoléculaire formelle obtenus. Des réactions impliquant des diènes électroniquement pauvres et neutres sont répertoriées. Il est également question de l'influence du solvant et de certains additifs sur la réaction. Une brève discussion des mécanismes réactionnels proposés pour expliquer la formation des différents produits observés est également exposée. Finalement, une étude de la barrière de rotation élevée des aminocarbènes peut être appréciée. Le troisième chapitre décrit les efforts effectués afin d'élargir l'étendue de la réaction et la compréhension du mécanisme réactionnel. Des réactions de
cycloaddition (4+1) formelle où les substrats présentent différents patrons de substitution sur le diène ainsi que sur le carbène y sont présentés.
Advisors/Committee Members: Spino, Claude (advisor).
Subjects/Keywords: Cyclopentène; Cycloaddition; Diène; Fischer; Aminocarbène
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
D. Lefebvre, L. (2012). Développement d'une réaction de cycloaddition (4+1) intramoléculaire formelle impliquant des aminocarbènes de chrome. (Masters Thesis). Université de Sherbrooke. Retrieved from http://hdl.handle.net/11143/5752
Chicago Manual of Style (16th Edition):
D. Lefebvre, Louis-Philippe. “Développement d'une réaction de cycloaddition (4+1) intramoléculaire formelle impliquant des aminocarbènes de chrome.” 2012. Masters Thesis, Université de Sherbrooke. Accessed May 06, 2021.
http://hdl.handle.net/11143/5752.
MLA Handbook (7th Edition):
D. Lefebvre, Louis-Philippe. “Développement d'une réaction de cycloaddition (4+1) intramoléculaire formelle impliquant des aminocarbènes de chrome.” 2012. Web. 06 May 2021.
Vancouver:
D. Lefebvre L. Développement d'une réaction de cycloaddition (4+1) intramoléculaire formelle impliquant des aminocarbènes de chrome. [Internet] [Masters thesis]. Université de Sherbrooke; 2012. [cited 2021 May 06].
Available from: http://hdl.handle.net/11143/5752.
Council of Science Editors:
D. Lefebvre L. Développement d'une réaction de cycloaddition (4+1) intramoléculaire formelle impliquant des aminocarbènes de chrome. [Masters Thesis]. Université de Sherbrooke; 2012. Available from: http://hdl.handle.net/11143/5752
University of Guelph
16.
Jack, Kelsey.
Investigations into the Ruthenium Catalyzed Ring Opening and Dimerization Reactions of Oxabicyclic Alkenes.
Degree: MS, Department of Chemistry, 2012, University of Guelph
URL: https://atrium.lib.uoguelph.ca/xmlui/handle/10214/4738
► Oxabicyclic alkenes have been the focus of many synthetic studies as they are versatile compounds which act as synthetic intermediates to produce a variety of…
(more)
▼ Oxabicyclic alkenes have been the focus of many synthetic studies as they are versatile compounds which act as synthetic intermediates to produce a variety of useful heterocyclic, carbocyclic and acyclic products. The nucleophilic ring opening reaction of oxabenzonorbornadiene was studied. Methanol was the primary nucleophile used throughout the investigation, however various other alcohol nucleophiles were also tested for their efficacy. The effects of substitution were explored, providing ring opened products in yields of up to 81%. The [2+2] cyclodimerization reaction of oxanorbornadienes was also examined providing the first examples of dimers of this kind. The scope was expanded to include other 2,3-diester oxanorbornadienes as well as various C1 substitutions. Changing the ester moiety did not affect the reaction, however the addition of a C1 alkyl substituent did result in lower yields. Moderate yields of up to 66% were obtained. Additionally, a new ruthenium complex was discovered in the process.
Advisors/Committee Members: Tam, William (advisor).
Subjects/Keywords: Cycloaddition; Oxabicyclic Alkenes; Dimerization; Cycloaddition; Ring Opening; Ruthenium
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Jack, K. (2012). Investigations into the Ruthenium Catalyzed Ring Opening and Dimerization Reactions of Oxabicyclic Alkenes. (Masters Thesis). University of Guelph. Retrieved from https://atrium.lib.uoguelph.ca/xmlui/handle/10214/4738
Chicago Manual of Style (16th Edition):
Jack, Kelsey. “Investigations into the Ruthenium Catalyzed Ring Opening and Dimerization Reactions of Oxabicyclic Alkenes.” 2012. Masters Thesis, University of Guelph. Accessed May 06, 2021.
https://atrium.lib.uoguelph.ca/xmlui/handle/10214/4738.
MLA Handbook (7th Edition):
Jack, Kelsey. “Investigations into the Ruthenium Catalyzed Ring Opening and Dimerization Reactions of Oxabicyclic Alkenes.” 2012. Web. 06 May 2021.
Vancouver:
Jack K. Investigations into the Ruthenium Catalyzed Ring Opening and Dimerization Reactions of Oxabicyclic Alkenes. [Internet] [Masters thesis]. University of Guelph; 2012. [cited 2021 May 06].
Available from: https://atrium.lib.uoguelph.ca/xmlui/handle/10214/4738.
Council of Science Editors:
Jack K. Investigations into the Ruthenium Catalyzed Ring Opening and Dimerization Reactions of Oxabicyclic Alkenes. [Masters Thesis]. University of Guelph; 2012. Available from: https://atrium.lib.uoguelph.ca/xmlui/handle/10214/4738
Université Paris-Sud – Paris XI
17.
Laurent, Grégory.
Réactions de cycloadditions énantiosélectives catalysées par des dérivés d’acides de Brønsted chiraux : Enantioselectives cycloadditions reactions catalyzed by chirals Brønsted acids derivatives.
Degree: Docteur es, Chimie, 2014, Université Paris-Sud – Paris XI
URL: http://www.theses.fr/2014PA112419
► Ces travaux de thèse avaient pour objectif la synthèse asymétrique d’hétérocycles énantioenrichis par des méthodes à hautes valeurs ajoutées. Pour cela des catalyseurs ont été…
(more)
▼ Ces travaux de thèse avaient pour objectif la synthèse asymétrique d’hétérocycles énantioenrichis par des méthodes à hautes valeurs ajoutées. Pour cela des catalyseurs ont été employés dans des réactions de cycloaddition. D’une part, l’organocatalyse asymétrique permet d’utiliser un matériel chiral peu coûteux en faible quantité pour générer des produits chiraux, d’autre part, les réactions de cycloadditions permettent une économie d’atome certaine et la création de plusieurs liaisons en une réaction.La première partie de cette thèse concerne des réactions de cycloadditions d’aza-Diels-Alder à demande inverse en électrons. Ces travaux mettent en jeu des 1-Azadiènes et des énecarbamates pour générer des tétrahydropyridines possédant 3 centres stéréogènes contigus.Les produits ont été obtenus sous la forme d’un seul diastéréomère avec de bons rendements et de bons excès énantiomérique. La modification des substrats sur diverses positions a été possible sans influencer l’efficacité de la réaction.Dans la seconde partie, une réaction de cycloaddition entre des quinones et des énecarbamates a été étudiée. L’utilisation d’un acide phosphorique à squelette SPINOL s’est révélée très efficaces, menant à des 2,3-Dihydrobenzofuranes optiquement actifs. Les produits sont isolés avec d’excellents rendements et excès énantiomériques, mais des ratios diastéréomériques faibles. Ces derniers peuvent être améliorés en engageant des énethiocarbamates.Une cascade réactionnelle peut aussi être effectuée en formant la quinone in situ à l’aide d’un réactif hypervalent iodé. L’étendue de notre cycloaddition ainsi que sa variante initié par du PIDA est conséquente mais reste encore à améliorer. Différentes hydroquinones seront ainsi évaluées. Les cycloadduits seront ultérieurement transformés de manière à valoriser cette méthodologie. Les configurations relatives et absolues des centres asymétriques formés seront déterminées avec précision par cliché de diffraction des rayons X. Ces pistes sont en cours d’étude et de réalisation au laboratoire.Enfin, la dernière partie concerne une réaction de cycloaddition 1,3-Dipolaire entre des nitrones et des énecarbamates. Si l’utilisation d’un acide phosphorique ne s’est pas révélée efficace, l’utilisation d’un phosphate de cuivre est en revanche convaincante. Initialement, la réaction a montré d’excellents résultats, malheureusement non reproductibles. Une optimisation rigoureuse a été nécessaire pour obtenir des résultats satisfaisants. Cette réaction nécessite une évaluation de son étendue vis-À-Vis des énecarbamates. Des transformations sont également envisagées pour valoriser cette méthodologie.
This thesis works were aimed the asymmetric synthesis of optically pure heterocycles by high added value methodology. On one hand, the asymmetric organocatalysis allows using an inexpensive chiral materials in small quantities to generate chiral products, on the other hand, the cycloaddition reactions allow atom economy and the creation of several bonds in one reaction.The first part of this thesis…
Advisors/Committee Members: Masson, Géraldine (thesis director).
Subjects/Keywords: Cycloaddition; Organocatalyse; Acide phosphorique; Énecarbamate; Cycloaddition; Organocatalysys; Phosphoric acid; Enecarbamate
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Laurent, G. (2014). Réactions de cycloadditions énantiosélectives catalysées par des dérivés d’acides de Brønsted chiraux : Enantioselectives cycloadditions reactions catalyzed by chirals Brønsted acids derivatives. (Doctoral Dissertation). Université Paris-Sud – Paris XI. Retrieved from http://www.theses.fr/2014PA112419
Chicago Manual of Style (16th Edition):
Laurent, Grégory. “Réactions de cycloadditions énantiosélectives catalysées par des dérivés d’acides de Brønsted chiraux : Enantioselectives cycloadditions reactions catalyzed by chirals Brønsted acids derivatives.” 2014. Doctoral Dissertation, Université Paris-Sud – Paris XI. Accessed May 06, 2021.
http://www.theses.fr/2014PA112419.
MLA Handbook (7th Edition):
Laurent, Grégory. “Réactions de cycloadditions énantiosélectives catalysées par des dérivés d’acides de Brønsted chiraux : Enantioselectives cycloadditions reactions catalyzed by chirals Brønsted acids derivatives.” 2014. Web. 06 May 2021.
Vancouver:
Laurent G. Réactions de cycloadditions énantiosélectives catalysées par des dérivés d’acides de Brønsted chiraux : Enantioselectives cycloadditions reactions catalyzed by chirals Brønsted acids derivatives. [Internet] [Doctoral dissertation]. Université Paris-Sud – Paris XI; 2014. [cited 2021 May 06].
Available from: http://www.theses.fr/2014PA112419.
Council of Science Editors:
Laurent G. Réactions de cycloadditions énantiosélectives catalysées par des dérivés d’acides de Brønsted chiraux : Enantioselectives cycloadditions reactions catalyzed by chirals Brønsted acids derivatives. [Doctoral Dissertation]. Université Paris-Sud – Paris XI; 2014. Available from: http://www.theses.fr/2014PA112419
University of Utah
18.
Lane, Timothy Karl.
The development of iron-catalyzed [2+2+2] cycloadditions to produce 6-membered nitrogen heterocycles.
Degree: PhD, Chemistry, 2015, University of Utah
URL: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/4058/rec/2441
► One of the greatest challenges in synthetic chemistry is the development of reactions that can efficiently afford target compounds without creating byproducts. One such class…
(more)
▼ One of the greatest challenges in synthetic chemistry is the development of reactions that can efficiently afford target compounds without creating byproducts. One such class of reactions are [2+2+2] cycloadditions. Here, three unsaturated coupling partners are combined to create six-membered rings, often with high regioselectivity, high yield, and no byproducts (i.e., secondary products). To further increase the attractiveness of these reactions, iron, a cheap and abundant catalyst, can be used. However, for the [2+2+2] synthesis of pyridines, a very important class of compounds, iron has traditionally been a very poor catalyst. By tethering unreactive nitriles to the more reactive alkynes, the first general iron-catalyzed [2+2+2] method to synthesize pyridines has been developed. This reactivity was further explored with the cycloaddition of diynes and cyanamides. Cyanamides demonstrated remarkable chemo- and regioselectivity. The three-component cycloaddition of terminal alkynes and a cyanamide could be performed with high yield and complete chemoselectivity. By combining aforementioned strategies of nitrile incorporation, the entirely novel cycloaddition of alkynenitriles and cyanamides has been developed. In this case, iron demonstrated reactivity that few [2+2+2] cycloaddition catalyst exhibited by incorporating multiple nitrogen atoms into the resulting 6-membered ring. Finally, isolation of presumed inorganic and organometallic intermediates provides a preliminary understanding of the mechanistic sequences involved in these iron-catalyzed [2+2+2] cycloadditions.
Subjects/Keywords: Catalyst; Cycloaddition; Inorganic; Organometallic; Pyridine; Pyrimidine
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Lane, T. K. (2015). The development of iron-catalyzed [2+2+2] cycloadditions to produce 6-membered nitrogen heterocycles. (Doctoral Dissertation). University of Utah. Retrieved from http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/4058/rec/2441
Chicago Manual of Style (16th Edition):
Lane, Timothy Karl. “The development of iron-catalyzed [2+2+2] cycloadditions to produce 6-membered nitrogen heterocycles.” 2015. Doctoral Dissertation, University of Utah. Accessed May 06, 2021.
http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/4058/rec/2441.
MLA Handbook (7th Edition):
Lane, Timothy Karl. “The development of iron-catalyzed [2+2+2] cycloadditions to produce 6-membered nitrogen heterocycles.” 2015. Web. 06 May 2021.
Vancouver:
Lane TK. The development of iron-catalyzed [2+2+2] cycloadditions to produce 6-membered nitrogen heterocycles. [Internet] [Doctoral dissertation]. University of Utah; 2015. [cited 2021 May 06].
Available from: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/4058/rec/2441.
Council of Science Editors:
Lane TK. The development of iron-catalyzed [2+2+2] cycloadditions to produce 6-membered nitrogen heterocycles. [Doctoral Dissertation]. University of Utah; 2015. Available from: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/4058/rec/2441
Université du Québec à Montréal
19.
Desjardins, Marc-André.
Cycloaddition 1,3-dipolaire intramoléculaire impliquant l'oxyde de nitrile et l'azoture comme dipôles et des 2-vinyloxazolidines dérivés de la noréphédrine.
Degree: 2008, Université du Québec à Montréal
URL: http://www.archipel.uqam.ca/1047/1/M10355.pdf
► L'utilisation de la réaction de cycloaddition 1,3-dipolaire permet la formation d'hétérocycles hautement fonctionnalisés. L'étude de cette réaction de manière intramoléculaire permet la formation de centres…
(more)
▼ L'utilisation de la réaction de cycloaddition 1,3-dipolaire permet la formation d'hétérocycles hautement fonctionnalisés. L'étude de cette réaction de manière intramoléculaire permet la formation de centres chiraux avec une excellente sélectivité. Un alcaloïde naturel, la noréphédrine, est utilisé comme gabarit chiral de départ pour l'insertion des groupements dipôle et dipolarophile nécessaires à la cyloaddition. L'adaptation d'une procédure développée par Roche Products LTD pour la formation d'un amide par l'addition d'un chlorure d'halogéno-alcanoyle sur l'amine de la noréphédrine a permis l'obtention d'amides pures sans le besoin de purification chromatographique. La condensation de ces N-alcanoylhalogénures avec un dérivé acétal de l'acroléine entraîne la formation d'une 2-vinyloxazolidine. L'optimisation des paramètres réactionnels a permis un contrôle parfait de la stéréochimie créé au nouveau centre chiral en C-2 (et la minimisation des produits secondaires formés). L'insertion de la fonction nitro nécessaire pour la cycloaddition intramoléculaire vers les isoxazolines a nécessité deux innovations différentes. Le passage par des intermédiaires iodés est préférable pour l'insertion des fonctions NO₂ et cette substitution a été optimisée afin de maximiser le ratio nitro/nitrite grâce à l'ajout de phloroglucinol. L'activation de dérivés nitro portés par des chaînes alkyles de longueur variables (nombre de carbones: 4 à 6) par la méthode de Mukaiyama a produit les cycloadduits isoxazolines. Toutefois, la longueur de la chaîne a un impact majeur sur la sélectivité de l'anneau 2-isoxazoline issu de la réaction. La cycloaddition à partir du dérivé nitrobutanoyle a formé un produit de régiochimie disubstitué 3,4, ce qui est inverse à la théorie des orbitales moléculaires pour les alcènes mono-substitués qui produisent généralement des isoxazolines substitués en 3,5 et d'une stéréochimie R* pour le centre chiral formé. Par contre, le dérivé nitropentanoyle forme un cycloadduit ayant une stéréochimie opposée S* tout en conservant la régiochimie du dérivé précédent. L'activation du dérivé nitrohexanoyle, a donné une isoxazoline de régiochimie normale disubstitué en 3,5 grâce à sa chaîne latérale plus longue qui permet la fixation de l'oxygène de l'oxyde de nitrile intermédiaire sur le carbone interne de la fonction alcène. La stéréochimie de ce cycloadduit est R*. L'étude de la longueur de la chaîne a donc montré dans un premier temps, une inversion de stéréochimie et ensuite une inversion de régiochimie. L'autre partie du projet consiste en l'utilisation d'une fonction azoture pour la cycloaddition menant aux triazolines. L'insertion de l'ion N₃‾ est aussi améliorée par la formation d'intermédiaires iodés et la cycloaddition nécessite un chauffage dépendant du dérivé. Les espèces triazolines de régiochimie normale 3,4 et de stéréochimie spécifique R* ont été générées. D'ailleurs, la stabilité des triazolines varie beaucoup et certaines d'entre elles doivent être utilisées sans purification. Leur activation subséquente…
Subjects/Keywords: Phénylpropanolamine; Cycloaddition; Oxyde de nitrile; Isoxazoline
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Desjardins, M. (2008). Cycloaddition 1,3-dipolaire intramoléculaire impliquant l'oxyde de nitrile et l'azoture comme dipôles et des 2-vinyloxazolidines dérivés de la noréphédrine. (Thesis). Université du Québec à Montréal. Retrieved from http://www.archipel.uqam.ca/1047/1/M10355.pdf
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Desjardins, Marc-André. “Cycloaddition 1,3-dipolaire intramoléculaire impliquant l'oxyde de nitrile et l'azoture comme dipôles et des 2-vinyloxazolidines dérivés de la noréphédrine.” 2008. Thesis, Université du Québec à Montréal. Accessed May 06, 2021.
http://www.archipel.uqam.ca/1047/1/M10355.pdf.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Desjardins, Marc-André. “Cycloaddition 1,3-dipolaire intramoléculaire impliquant l'oxyde de nitrile et l'azoture comme dipôles et des 2-vinyloxazolidines dérivés de la noréphédrine.” 2008. Web. 06 May 2021.
Vancouver:
Desjardins M. Cycloaddition 1,3-dipolaire intramoléculaire impliquant l'oxyde de nitrile et l'azoture comme dipôles et des 2-vinyloxazolidines dérivés de la noréphédrine. [Internet] [Thesis]. Université du Québec à Montréal; 2008. [cited 2021 May 06].
Available from: http://www.archipel.uqam.ca/1047/1/M10355.pdf.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Desjardins M. Cycloaddition 1,3-dipolaire intramoléculaire impliquant l'oxyde de nitrile et l'azoture comme dipôles et des 2-vinyloxazolidines dérivés de la noréphédrine. [Thesis]. Université du Québec à Montréal; 2008. Available from: http://www.archipel.uqam.ca/1047/1/M10355.pdf
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Texas A&M University
20.
Wang, Xiaoshan.
The Nitrilimine-Alkene Cycloaddition Mechanism and Phage-displayed Cyclic Peptide Libraries for Drug Discovery.
Degree: PhD, Chemistry, 2018, Texas A&M University
URL: http://hdl.handle.net/1969.1/173491
► This study is composed of two parts. In the first part, we discussed nitrilimine-alkene cycloaddition for protein labeling. The mechanism of this nitrilimine-alkene cycloaddition was…
(more)
▼ This study is composed of two parts. In the first part, we discussed nitrilimine-alkene
cycloaddition for protein labeling. The mechanism of this nitrilimine-alkene
cycloaddition was proposed, and thereby the best experimental condition for this protein labeling approach was investigated. The transient formation of nitrilimine in aqueous conditions is greatly influenced by pH and chloride. In basic conditions (pH 10) with no chloride, a diarylnitrilimine precursor readily ionizes to form diarylnitrilimine that reacts almost instantly with an acrylamide-containing protein and fluorescently labels it.
In the second part, a novel method for the synthesis of phage-displayed cyclic peptide libraries is presented. Cyclic peptide drugs are appealing in the drug discovery research area due to their unique advantages including high affinity, high specificity, low toxicity, and high cellular and serum stability. In order to identify cyclic peptides as therapeutic agents, during my graduate study I have developed a phage display-based methodology that integrates the genetic noncanonical amino acid (ncAA) mutagenesis technique for the synthesis of novel phage-displayed cyclic peptides through simultaneous 1,4-addition between a cysteine thiol group and acrylamide moiety in Nε -acryloyl-lysine (AcrK), a ncAA. Both cysteine and AcrK are genetically coded. The success of using a cysteine and an AcrK to cyclic a peptide in a model protein and phages was validated by various approaches. In order to afford a library, a phage-displayed cyclic peptide library was constructed by inserting a consecutive but sequence-randomized 6-mer peptide flanked by an amino side cysteine and a carboxyl side AcrK. Panning of the synthesized phage-displayed cyclic peptide library was performed against two target proteins that are tobacco etch virus (TEV) protease and histone deacetylase 8 (HDAC8). A lot of high-affinity phage clones were isolated and collected. DNA sequencing of these selected clones led to the identification of several peptides that potentially inhibit TEV protease and HDAC8. To confirm their potencies as inhibitors, abundant peptides and their fluorophore-conjugated derivatives were synthesized through solid-phase peptide synthesis (SPPS). Measurements of fluorescence polarization change and IC50 value of these peptides when they bound to TEV protease and HDAC8 were performed.
Overall, we have mechanistically characterized the nitrilimine-alkene
cycloaddition reaction and developed a novel approach for the synthesis of phage-displayed cyclic peptide libraries. The selection of displayed peptides against TEV protease and HDAC8 has resulted in multiple peptides that display high potencies against these two enzymes.
Advisors/Committee Members: Liu, Wenshe (advisor), Begley, Tadhg (committee member), Lindahl, Paul (committee member), Raushel, Frank (committee member).
Subjects/Keywords: nitrilimine-alkene cycloaddition; cyclic peptide; HDAC8 inhibitor
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Wang, X. (2018). The Nitrilimine-Alkene Cycloaddition Mechanism and Phage-displayed Cyclic Peptide Libraries for Drug Discovery. (Doctoral Dissertation). Texas A&M University. Retrieved from http://hdl.handle.net/1969.1/173491
Chicago Manual of Style (16th Edition):
Wang, Xiaoshan. “The Nitrilimine-Alkene Cycloaddition Mechanism and Phage-displayed Cyclic Peptide Libraries for Drug Discovery.” 2018. Doctoral Dissertation, Texas A&M University. Accessed May 06, 2021.
http://hdl.handle.net/1969.1/173491.
MLA Handbook (7th Edition):
Wang, Xiaoshan. “The Nitrilimine-Alkene Cycloaddition Mechanism and Phage-displayed Cyclic Peptide Libraries for Drug Discovery.” 2018. Web. 06 May 2021.
Vancouver:
Wang X. The Nitrilimine-Alkene Cycloaddition Mechanism and Phage-displayed Cyclic Peptide Libraries for Drug Discovery. [Internet] [Doctoral dissertation]. Texas A&M University; 2018. [cited 2021 May 06].
Available from: http://hdl.handle.net/1969.1/173491.
Council of Science Editors:
Wang X. The Nitrilimine-Alkene Cycloaddition Mechanism and Phage-displayed Cyclic Peptide Libraries for Drug Discovery. [Doctoral Dissertation]. Texas A&M University; 2018. Available from: http://hdl.handle.net/1969.1/173491
21.
Thomas, David Robert.
Efforts towards understanding the nickel catalyzed cycloaddition of ciynes and nitriles to make pyridines.
Degree: MS, Chemistry, 2014, University of Utah
URL: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2883/rec/842
► Efforts towards understanding the nickel catalyzed cycloaddition of diynes and nitriles to make pyridines are described. During the course of this mechanistic study, a previously…
(more)
▼ Efforts towards understanding the nickel catalyzed cycloaddition of diynes and nitriles to make pyridines are described. During the course of this mechanistic study, a previously uncharacterized class of nickel-nitrile-NHC (N-heterocyclic carbene) dimers, which display cooperative η1 and η2 binding modes of the nitrile to nickel, were discovered. Crystal structures were obtained for select dimers. These dimers proved catalytically competent in the cycloaddition reaction. Pseudo first order kinetics revealed that the reaction was first order in dimer while being zero order in NHC ligand, nitrile, and diyne. While stoichiometric reactions with dimer and diyne in the absence of nitrile did give product, largely improved yields were observed in the presence of free nitrile. Stoichiometric competition studies utilizing various identities of free nitriles and dimers indicated a preference for incorporation of free nitrile into the product versus the dimer-bound nitrile. The results of this study suggest a mechanism involving partial dimer opening as the rate-determining step. This is then followed by nitrile binding, which precedes oxidative coupling with diyne.
Subjects/Keywords: Cycloaddition; Pyridine
…x5B;1a], kobs vs [IPr], and kobs vs [MeCN] for the
cycloaddition of… …and angles in Figure 3.
Dimer 3 was found to catalyze the cycloaddition of nitriles and… …x5D; for the
cycloaddition of 4 at 0 °C in C7D8
10
Scheme 5. Possible mechanistic… …cycloaddition of nitriles and diynes to form pyridines. Kinetic studies showed a
dependence of the… …28.8, 24.8, 23.7.19
Cycloaddition catalyzed by 3a. A stock solution of 3a was prepared by…
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Thomas, D. R. (2014). Efforts towards understanding the nickel catalyzed cycloaddition of ciynes and nitriles to make pyridines. (Masters Thesis). University of Utah. Retrieved from http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2883/rec/842
Chicago Manual of Style (16th Edition):
Thomas, David Robert. “Efforts towards understanding the nickel catalyzed cycloaddition of ciynes and nitriles to make pyridines.” 2014. Masters Thesis, University of Utah. Accessed May 06, 2021.
http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2883/rec/842.
MLA Handbook (7th Edition):
Thomas, David Robert. “Efforts towards understanding the nickel catalyzed cycloaddition of ciynes and nitriles to make pyridines.” 2014. Web. 06 May 2021.
Vancouver:
Thomas DR. Efforts towards understanding the nickel catalyzed cycloaddition of ciynes and nitriles to make pyridines. [Internet] [Masters thesis]. University of Utah; 2014. [cited 2021 May 06].
Available from: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2883/rec/842.
Council of Science Editors:
Thomas DR. Efforts towards understanding the nickel catalyzed cycloaddition of ciynes and nitriles to make pyridines. [Masters Thesis]. University of Utah; 2014. Available from: http://content.lib.utah.edu/cdm/singleitem/collection/etd3/id/2883/rec/842
22.
Vanbeselaere, Jorick.
Analyses structurales et métaboliques de la sialylation des vertébrés : Structural and metabolic analysis in the sialylation of vertebrates.
Degree: Docteur es, Aspects moléculaires et cellulaires de la biologie, 2013, Université Lille I – Sciences et Technologies
URL: http://www.theses.fr/2013LIL10153
► Les travaux présentés explorent la diversité structurale des glycannes dans l’organisme modèle du Poisson Zèbre et analysent la régulation des sialoconjugués lors d’évènements physiopathologiques particuliers.…
(more)
▼ Les travaux présentés explorent la diversité structurale des glycannes dans l’organisme modèle du Poisson Zèbre et analysent la régulation des sialoconjugués lors d’évènements physiopathologiques particuliers. La première partie de mes travaux vise à étendre nos connaissances structurales sur la distribution des glycannes à l’échelle cellulaire et tissulaire grâce à l’étude d’un modèle majeur de vertébré, le poisson zèbre. Ces travaux s’inscrivent dans une optique de recherche fondamentale pour établir la première carte de glycosylation (glycosphingolipides ; N- et O-glycannes) des organes du poisson zèbre adulte. A terme, ces résultats permettront de mieux appréhender les relations structures-fonctions des glycannes au niveau des organismes entiers. La seconde partie de mes travaux se focalise sur le suivi structural et métabolique de la sialylation. Une première stratégie est basée sur l’utilisation d’un mime-alcyné de l’acide sialique que nous pouvons coupler à un fluorophore-azidé par « click-chemistry » pour visualiser les sialoconjugués en microscopie. Ainsi, nous avons étudié le métabolisme de l’acide sialique des fibroblastes de patients atteints de Maladie Congénitale de la Glycosylation ou pour suivre la métabolisation de l’acide sialique après une infection par le parasite intracellulaire Toxoplasma gondii. Une seconde stratégie s’intéresse à la régulation de la sialylation par des analyses structurales lors d’une infection parasitaire par Trypanosoma cruzii ou lors de la surexpression d’une sialyltransferase dans la lignée cellulaire MCF-7. Ces études révèlent d’importantes variations dans l’expression des sialoglycoconjugués.
Our studies investigated the structural diversity of glycans in zebrafish model organism and analyzed the regulation of sialoconjuguates during specific pathophysiological events. First part of my work intends to expand our structural knowledge about the organisation of glycans at the cellular and tissue levels through the study of a major vertebrate model, the zebrafish. This study aims to establish the first map of glycosylation in zebrafish, including profiles of glycosphingolipids as well as N- and O-glycans of glycoproteins. These data reveal numerous novel structures, including oligofucosylated and oligosialylated glycosphingolipids, and inform us about the organization of glycans within each organ. These results will provide new insight into the structure-function relationships of glycans in whole organisms. Second part of my work focuses on the structural and metabolic monitoring of sialylation. One of the deployed strategies is based on the use of an alkyne analogue of sialic acid and that can specially bind to a fluorophore by click-chemistry for monitoring the sialoconjugates by fluorescence microscopy. This strategy has been implemented to study sialic acid metabolism of fibroblasts from patients with congenital disease of the glycosylation or to follow the sialic acid metabolism after infection with the intracellular parasite Toxoplasma gondii. A second strategy…
Advisors/Committee Members: Guérardel, Yann (thesis director).
Subjects/Keywords: Glycome; Cycloaddition cuivre-azide-alcyne; 572.68
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Vanbeselaere, J. (2013). Analyses structurales et métaboliques de la sialylation des vertébrés : Structural and metabolic analysis in the sialylation of vertebrates. (Doctoral Dissertation). Université Lille I – Sciences et Technologies. Retrieved from http://www.theses.fr/2013LIL10153
Chicago Manual of Style (16th Edition):
Vanbeselaere, Jorick. “Analyses structurales et métaboliques de la sialylation des vertébrés : Structural and metabolic analysis in the sialylation of vertebrates.” 2013. Doctoral Dissertation, Université Lille I – Sciences et Technologies. Accessed May 06, 2021.
http://www.theses.fr/2013LIL10153.
MLA Handbook (7th Edition):
Vanbeselaere, Jorick. “Analyses structurales et métaboliques de la sialylation des vertébrés : Structural and metabolic analysis in the sialylation of vertebrates.” 2013. Web. 06 May 2021.
Vancouver:
Vanbeselaere J. Analyses structurales et métaboliques de la sialylation des vertébrés : Structural and metabolic analysis in the sialylation of vertebrates. [Internet] [Doctoral dissertation]. Université Lille I – Sciences et Technologies; 2013. [cited 2021 May 06].
Available from: http://www.theses.fr/2013LIL10153.
Council of Science Editors:
Vanbeselaere J. Analyses structurales et métaboliques de la sialylation des vertébrés : Structural and metabolic analysis in the sialylation of vertebrates. [Doctoral Dissertation]. Université Lille I – Sciences et Technologies; 2013. Available from: http://www.theses.fr/2013LIL10153
23.
Nöcker, Christina.
Synthese von Naturstoff-basierten Substanzbibliotheken.
Degree: 2017, Technische Universität Dortmund
URL: http://dx.doi.org/10.17877/DE290R-17961
► The following thesis describes the synthesis of natural product inspired compound libraries. The synthesis of depsipeptides Chondramid C and analogues was conducted. The synthesis strategy…
(more)
▼ The following thesis describes the synthesis of natural product inspired compound libraries. The synthesis of depsipeptides Chondramid C and analogues was conducted. The synthesis strategy was based on an efficient solid phase synthesis with subsequent metathesis reaction to the cyclic products. The solid supported linker was constructed via Wittig olefination. On solid support the polypeptide and polyketide structures were esterified. An amidation on solid support linked the polypeptide part with the polyketide part. After cleavage from the solid support the depsipeptides were formed via a ring closing metathesis reaction. A compound library based on the picolinamide and benzamide scaffold was synthesized. Differently substituted carboxylic acids reacted with different amines forming an amide bond. The compound library was tested for its biological activity within a cooperation with genetic, biochemical and in silico investigations. Potent Sec14p
inhibitors were found from the compound library. A compound library based on the oxazolidinone scaffold was synthesized. N-acylated auxiliaries, hydrogenated alkylated oxazolidinones, oxazolidinones without stereo center at the side chain and syn-aldol products were synthesized. By means of an asymmetric alkylation with sodium hexamethyldisilazide different alkylated oxazolidinones were constructed. The compound library was tested within a cooperation in genetic and biochemical assays. A weak Sec14p inhibitor was found. In contrast to intermolecular 1,3-dipolar cycloadditions intramolecular enantioselective 1,3-dipolar cycloadditions are virtually unexplored. In this thesis an enantioselective intramolecular 1,3-dipolar
cycloaddition from azomethine ylides was developed constructing quinoline-pyrrolidinyl-spirooxindoles. First N-Aryl-amides were synthesized. After deprotection the Schiff base was established in situ, which reacted in a subsequent copper(II) catalyzed intramolecular
cycloaddition forming spiro compounds. With a cell painting assay a novel bioactivity was found for this chemotype.
Advisors/Committee Members: Waldmann, Herbert (advisor), Summerer, Daniel (referee).
Subjects/Keywords: Cyclodepsipeptide; Sec14p; Cycloaddition; Organische Synthese; 570; 540
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Nöcker, C. (2017). Synthese von Naturstoff-basierten Substanzbibliotheken. (Doctoral Dissertation). Technische Universität Dortmund. Retrieved from http://dx.doi.org/10.17877/DE290R-17961
Chicago Manual of Style (16th Edition):
Nöcker, Christina. “Synthese von Naturstoff-basierten Substanzbibliotheken.” 2017. Doctoral Dissertation, Technische Universität Dortmund. Accessed May 06, 2021.
http://dx.doi.org/10.17877/DE290R-17961.
MLA Handbook (7th Edition):
Nöcker, Christina. “Synthese von Naturstoff-basierten Substanzbibliotheken.” 2017. Web. 06 May 2021.
Vancouver:
Nöcker C. Synthese von Naturstoff-basierten Substanzbibliotheken. [Internet] [Doctoral dissertation]. Technische Universität Dortmund; 2017. [cited 2021 May 06].
Available from: http://dx.doi.org/10.17877/DE290R-17961.
Council of Science Editors:
Nöcker C. Synthese von Naturstoff-basierten Substanzbibliotheken. [Doctoral Dissertation]. Technische Universität Dortmund; 2017. Available from: http://dx.doi.org/10.17877/DE290R-17961
Colorado State University
24.
Dalton, Derek M.
Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions.
Degree: PhD, Chemistry, 2013, Colorado State University
URL: http://hdl.handle.net/10217/80142
► Described herein are mechanistic studies and ligand development for Rh(I) catalyzed [2+2+2] cycloaddition reactions of alkene tethered isocyanates and exogenous alkynes. A mechanistic hypothesis has…
(more)
▼ Described herein are mechanistic studies and ligand development for Rh(I) catalyzed [2+2+2]
cycloaddition reactions of alkene tethered isocyanates and exogenous alkynes. A mechanistic hypothesis has been proposed and supported through experiment. Novel perfluoroaryl Taddol phosphoramidite ligands were developed based on the mechanistic hypothesis. Improvements in product and enantioselectivity were found using the perfluoroaryl Taddol phosphoramidite ligand, CKphos. This catalyst system was studied by NMR, X-ray and DFT calculations. Rh(I)-C6F5 and Co(-1)-C6F5 interactions were found in the course of studying the CKphos catalysts. The Rh-CKphos catalyst system was used in the synthesis of the tricyclic core structure of the cylindricine and lepadiformine alkaloids. Finally a Zn(II)-catalyzed [4+2]
cycloaddition of 1- azabutadienes and nitro olefins was discovered and developed as an efficient and selective means to synthesize tetrahydropyridines.
Advisors/Committee Members: Rovis, Tomislav (advisor), Wood, John L. (committee member), Kennan, Alan J. (committee member), Rappé, Anthony K. (committee member), Snow, Christopher D. (committee member).
Subjects/Keywords: cycloaddition; zinc; rhodium; enantioselective; heterocycles; catalysis
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Dalton, D. M. (2013). Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/80142
Chicago Manual of Style (16th Edition):
Dalton, Derek M. “Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions.” 2013. Doctoral Dissertation, Colorado State University. Accessed May 06, 2021.
http://hdl.handle.net/10217/80142.
MLA Handbook (7th Edition):
Dalton, Derek M. “Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions.” 2013. Web. 06 May 2021.
Vancouver:
Dalton DM. Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions. [Internet] [Doctoral dissertation]. Colorado State University; 2013. [cited 2021 May 06].
Available from: http://hdl.handle.net/10217/80142.
Council of Science Editors:
Dalton DM. Mechanistic investigations and ligand development for rhodium catalyzed [2+2+2] and zinc catalyzed [4+2] cycloadditions. [Doctoral Dissertation]. Colorado State University; 2013. Available from: http://hdl.handle.net/10217/80142
University of Ottawa
25.
Rochon, Alexandra.
Cycloaddition Reactions of Ni(0) Difluorocarbene Complexes: Investigating the Formation of Various Perfluorometallacycles
.
Degree: 2019, University of Ottawa
URL: http://hdl.handle.net/10393/39026
► Formation of carbon–fluorine and carbon–fluoroalkyl bonds via transition metal complexes represents an efficient synthetic route towards a wide array of valuable fluorinated organic compounds and…
(more)
▼ Formation of carbon–fluorine and carbon–fluoroalkyl bonds via transition metal complexes represents an efficient synthetic route towards a wide array of valuable fluorinated organic compounds and fluorinated metallacycles offer a potentially green and atom economical pathway towards these functionalized fluorocarbons. This thesis is focused on cycloaddition reactions of Ni=CF2 complexes with fluoroalkenes (FAs) and acetylenes.
Cycloaddition reactions of the FAs vinylidene fluoride (CF2=CH2) and perfluoro(methyl vinyl ether) [CF2=CF(OCF3)] with the electron-rich Ni(0) fluorocarbene, Ni=CF2[P(OMe)3](dppe) affords stable metallacyclobutane complexes, likely through a 1,4-diradical mechanism previously investigated for analogous reactions using computational chemistry. With CF2=CHF (TrFE), however, the observed products are the C3 alkene E-CHF=CF(CF3) and the metallacyclopentane complex, Ni(C4H2F6)(dppe), derived from oxidative coupling of two additional equivalents of TrFE. It is proposed that the instability of the initially formed metallacyclobutane gives rise to a 2,1-F shift, yielding the C3 alkene complex. Reaction of the latter with excess TrFE then liberates the C3 alkene, forming the TrFE alkene complex followed by the observed metallacyclopentane product. In the reaction of 1a with chlorotrifluoroethylene (CF2=CFCl) a single regioisomer of the metallacyclobutane is observed, but reacts further in THF solvent via α-Cl migration to Ni, affording the tetrafluoroallyl complex, NiCl(CF2CF=CFH), in which one F has been replaced by a hydrogen. Finally, reaction of 1a with hexafluoropropene [CF2=CF(CF3), HFP] takes an unprecedented turn, affording the Ni trifluoromethyl perfluoroalkenyl complex from formal transfer of one F from HFP to the Ni=CF2 moiety.
The capability of 1a to perform cycloaddition with a broader substrate scope was investigating by reacting it with terminal aryl-acetylenes of varying electronic parameters. Reaction of 1a with 1.5 equivalents of 4-R-phenylacetylene afforded the expected difluorometallacyclobutenes (R = H, Cl, tBu). Further observation revealed a second acetylene insertion to yield a nickelacyclohexadiene in the first example of a 4- to 6-membered ring expansion of perfluorometallacycles. The six-membered metallacycle then undergoes reductive elimination to furnish a difluorocyclopentadiene. The electronic parameters of the aryl-acetylene substrate play a dramatic role in the selectivity of product formation. The more electron-donating substrates 4-tert-butylphenylacetylene and 1-hexyne stabilize the metallacyclobutene, while the electron-withdrawing 4-chlorophenylacetylene affords a more reactive metallacyclobutene making it more prone to the second acetylene insertion. Phenylacetylene represented a middle-ground between the two systems and proved effective for further characterization studies. The electronic effect of the surrounding ancillary ligand system was also studied by substituting dppe in 1a for P(OMe)3 and dipe to give analogous Ni(0) difluorocarbene complexes 1b and…
Subjects/Keywords: Cycloaddition reactions;
Carbon-fluoroalkyl;
Carbon-fluorine
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Rochon, A. (2019). Cycloaddition Reactions of Ni(0) Difluorocarbene Complexes: Investigating the Formation of Various Perfluorometallacycles
. (Thesis). University of Ottawa. Retrieved from http://hdl.handle.net/10393/39026
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Rochon, Alexandra. “Cycloaddition Reactions of Ni(0) Difluorocarbene Complexes: Investigating the Formation of Various Perfluorometallacycles
.” 2019. Thesis, University of Ottawa. Accessed May 06, 2021.
http://hdl.handle.net/10393/39026.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Rochon, Alexandra. “Cycloaddition Reactions of Ni(0) Difluorocarbene Complexes: Investigating the Formation of Various Perfluorometallacycles
.” 2019. Web. 06 May 2021.
Vancouver:
Rochon A. Cycloaddition Reactions of Ni(0) Difluorocarbene Complexes: Investigating the Formation of Various Perfluorometallacycles
. [Internet] [Thesis]. University of Ottawa; 2019. [cited 2021 May 06].
Available from: http://hdl.handle.net/10393/39026.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Rochon A. Cycloaddition Reactions of Ni(0) Difluorocarbene Complexes: Investigating the Formation of Various Perfluorometallacycles
. [Thesis]. University of Ottawa; 2019. Available from: http://hdl.handle.net/10393/39026
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Boston College
26.
Fort, Eric Henry.
Developing Methods for Growing Single-Chirality Carbon
Nanotubes and Other Aromatic Systems.
Degree: PhD, Chemistry, 2010, Boston College
URL: http://dlib.bc.edu/islandora/object/bc-ir:101647
► The work described herein stems from an effort to develop a method for growing single-chirality carbon nanotubes from small hydrocarbon templates using a Diels-Alder cycloaddition/rearomatization…
(more)
▼ The work described herein stems from an effort to
develop a method for growing single-chirality carbon nanotubes from
small hydrocarbon templates using a Diels-Alder
cycloaddition/rearomatization strategy. Current technologies are
incapable of producing significant amounts of homogeneous carbon
nanotubes; therefore, much research has been put into the
development of aromatic templates (belts and bowls), from which one
type of nanotube might be grown (Chapter 1). Since no such
functional template had yet been synthesized, the work in this
dissertation developed reagents and methods for forming new benzene
rings on aromatic test systems that would be analogous to the rim
of a growing nanotube (Chapters 2 and 4). Theoretical
investigations relating to nanotube dimensions (Chapter 3) were
undertaken and paired with experimental work that would take into
consideration the changing properties of growing tubes (Chapter 5).
The test systems used for discovering new reagents for growth also
became functional platforms for studies of new reactivity of
polycyclic aromatic hydrocarbons (PAHs), such as bay-region
oxidation (Chapter 6) and progress toward the synthesis of soluble
graphene ribbons (Chapter 7). This PAH work also resulted in the
observation of unique solid state properties in the crystal form
(Chapter 8) and novel reactivity, generating five-membered rings by
Scholl reactions of tethered PAHs (Chapter 9). Additional
considerations for future nanotube templates and fullerene
precursors also bore scrutiny (Chapter 10).
Advisors/Committee Members: Lawrence T. Scott (Thesis advisor).
Subjects/Keywords: Armchair; Carbon Nanotubes; cycloaddition; Diels-Alder; rearomatization
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Fort, E. H. (2010). Developing Methods for Growing Single-Chirality Carbon
Nanotubes and Other Aromatic Systems. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:101647
Chicago Manual of Style (16th Edition):
Fort, Eric Henry. “Developing Methods for Growing Single-Chirality Carbon
Nanotubes and Other Aromatic Systems.” 2010. Doctoral Dissertation, Boston College. Accessed May 06, 2021.
http://dlib.bc.edu/islandora/object/bc-ir:101647.
MLA Handbook (7th Edition):
Fort, Eric Henry. “Developing Methods for Growing Single-Chirality Carbon
Nanotubes and Other Aromatic Systems.” 2010. Web. 06 May 2021.
Vancouver:
Fort EH. Developing Methods for Growing Single-Chirality Carbon
Nanotubes and Other Aromatic Systems. [Internet] [Doctoral dissertation]. Boston College; 2010. [cited 2021 May 06].
Available from: http://dlib.bc.edu/islandora/object/bc-ir:101647.
Council of Science Editors:
Fort EH. Developing Methods for Growing Single-Chirality Carbon
Nanotubes and Other Aromatic Systems. [Doctoral Dissertation]. Boston College; 2010. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101647
University of Bath
27.
Moss, William Osburn.
Novel amino acid synthons based on ketene thioacetals.
Degree: PhD, 1990, University of Bath
URL: https://researchportal.bath.ac.uk/en/studentthesis/novel-amino-acid-synthons-based-on-ketene-thioacetals(eadd46cf-05cb-475a-851a-074ee84679ce).html
;
https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.253997
Subjects/Keywords: 547; Cycloaddition reactions
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Moss, W. O. (1990). Novel amino acid synthons based on ketene thioacetals. (Doctoral Dissertation). University of Bath. Retrieved from https://researchportal.bath.ac.uk/en/studentthesis/novel-amino-acid-synthons-based-on-ketene-thioacetals(eadd46cf-05cb-475a-851a-074ee84679ce).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.253997
Chicago Manual of Style (16th Edition):
Moss, William Osburn. “Novel amino acid synthons based on ketene thioacetals.” 1990. Doctoral Dissertation, University of Bath. Accessed May 06, 2021.
https://researchportal.bath.ac.uk/en/studentthesis/novel-amino-acid-synthons-based-on-ketene-thioacetals(eadd46cf-05cb-475a-851a-074ee84679ce).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.253997.
MLA Handbook (7th Edition):
Moss, William Osburn. “Novel amino acid synthons based on ketene thioacetals.” 1990. Web. 06 May 2021.
Vancouver:
Moss WO. Novel amino acid synthons based on ketene thioacetals. [Internet] [Doctoral dissertation]. University of Bath; 1990. [cited 2021 May 06].
Available from: https://researchportal.bath.ac.uk/en/studentthesis/novel-amino-acid-synthons-based-on-ketene-thioacetals(eadd46cf-05cb-475a-851a-074ee84679ce).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.253997.
Council of Science Editors:
Moss WO. Novel amino acid synthons based on ketene thioacetals. [Doctoral Dissertation]. University of Bath; 1990. Available from: https://researchportal.bath.ac.uk/en/studentthesis/novel-amino-acid-synthons-based-on-ketene-thioacetals(eadd46cf-05cb-475a-851a-074ee84679ce).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.253997
University of Western Ontario
28.
Farhadpour, Bahareh.
Doubly Bonded Derivatives of Si and Ge: Cycloaddition Reactions and Polymer Chemistry.
Degree: 2017, University of Western Ontario
URL: https://ir.lib.uwo.ca/etd/4606
► (Di)tetrelenes are a fundamental class of unsaturated Group 14 compounds and play a central role in the synthesis of functional Group 14 compounds. The objective…
(more)
▼ (Di)tetrelenes are a fundamental class of unsaturated Group 14 compounds and play a central role in the synthesis of functional Group 14 compounds. The objective of this research was to investigate the various aspects of group 14 (di)tetrelenes (R2M=ER2, M = Si, Ge, and E = C, Si, Ge) reactivity.
The addition of a series of nitrone and nitro compounds to the group 14 (di)tetrelenes
Mes2Si=SiMes2, Mes2Ge=GeMes2 and Mes2Ge=CH(CH2-t-Bu), was examined. In general, the addition of the 1,3-dipolar nitrogen oxides to the (di)tetrelene gave 5-membered ring adducts via a formal [3+2] cycloaddition where the (di)tetrelene acts as the 2p component and the nitro/nitrone act as the 4p component. In some cases, the ring underwent rearrengment or cleavage to give secondary products.
Reactivity of (di)tetrelenes toward R2HP=O derivatives, where R = Ph, OPh, OCH3, and R3P:,where R = OCH3,to tetramesityldigermene 1.2 and/or the germene 1.1 is reported in an effort to give a broader understanding of the chemistry of the addition of phosphine oxides to (di)tetrelenes. In general, a 1,2-adduct is formed which appears to be derived from the isomeric hydroxyphosphines. Notably, the phosphine oxides are reduced during the course of the reaction. A comparison to the analogous chemistry of alkenes and surface digermenes is made.
A variety of alkyllithium (R = Me, Bu, t-Bu) reagents and potassium tert-butoxide were added to the highly reactive silene Mes2Si=CHCH2t-Bu and the germene Mes2Ge=CHCH2t-Bu, in diethyl ether. 1,2-Addition products were obtained regioselectively and in good yield after treatment with a weak acid with no evidence for any rearrangement products and no polymerization was observed. The reactivity of the silene and germene toward organometallic reagents is compared to previous studies of analogous silenes and germenes.
The characterization of polysilenes and polygermenes derived from the anionic polymerization of silenes and germenes, respectively, is reported. The molecular weight of the polygermene was determined by static light scattering (SLS) in THF which showed that Mw to be 41500 g mol-1. The Mw determined by SLS was compared to the data obtained by GPC. Characterization of polysilene and polygermene by ESI-MS revealed the presence of oligomers (n < 10) of the polytetrelenes. The mass spectral data also reveal the presence of R-Ge and C-H end groups, consistent with a chain growth mechanism where the R group is derived from the anionic initiator. NMR spectroscopic analysis of the polysilene provided further evidence of a chain growth mechanism for the anionic polymerization of the silene without rearrangement during the polymerization.
Subjects/Keywords: Silene; Germene; Polygermene; Polysilene; Cycloaddition; Chemistry
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Farhadpour, B. (2017). Doubly Bonded Derivatives of Si and Ge: Cycloaddition Reactions and Polymer Chemistry. (Thesis). University of Western Ontario. Retrieved from https://ir.lib.uwo.ca/etd/4606
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Chicago Manual of Style (16th Edition):
Farhadpour, Bahareh. “Doubly Bonded Derivatives of Si and Ge: Cycloaddition Reactions and Polymer Chemistry.” 2017. Thesis, University of Western Ontario. Accessed May 06, 2021.
https://ir.lib.uwo.ca/etd/4606.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
MLA Handbook (7th Edition):
Farhadpour, Bahareh. “Doubly Bonded Derivatives of Si and Ge: Cycloaddition Reactions and Polymer Chemistry.” 2017. Web. 06 May 2021.
Vancouver:
Farhadpour B. Doubly Bonded Derivatives of Si and Ge: Cycloaddition Reactions and Polymer Chemistry. [Internet] [Thesis]. University of Western Ontario; 2017. [cited 2021 May 06].
Available from: https://ir.lib.uwo.ca/etd/4606.
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
Council of Science Editors:
Farhadpour B. Doubly Bonded Derivatives of Si and Ge: Cycloaddition Reactions and Polymer Chemistry. [Thesis]. University of Western Ontario; 2017. Available from: https://ir.lib.uwo.ca/etd/4606
Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation
University of Victoria
29.
Morrow, Krista Maria Elena.
Phosphorus-containing ruthenacycles: exploring their potential in processes relevant to hydrophosphination.
Degree: Dept. of Chemistry, 2012, University of Victoria
URL: http://hdl.handle.net/1828/3890
► Phosphorus-containing metallacycles formed from the [2+2] cycloaddition of unsaturated substrates at the Ru-P π-bond of [Ru(η5-indenyl)(PCy2)(PPh3)] (2) were examined as possible intermediates relevant to hydrophosphination.…
(more)
▼ Phosphorus-containing metallacycles formed from the [2+2]
cycloaddition of unsaturated substrates at the Ru-P π-bond of [Ru(η5-indenyl)(PCy2)(PPh3)] (2) were examined as possible intermediates relevant to hydrophosphination. Reagents, intermediates, products, and by-products involved in the [2+2]
cycloaddition were identified and analyzed for reactivity and stability. The products, metallacycles of the form [Ru(η5-indenyl)(κ2-RCHCH2PCy2)(PPh3)] (4), were found to undergo facile cycloreversion. An ethylene η2-coordination adduct was directly observed by low temperature 31P{1H} NMR as an intermediate in the [2+2]
cycloaddition mechanism. Steric and electronic effects of alkene substituents on metallacycle formation and selectivity were investigated in detail through rate constant and activation parameter determination, as well as collaborative computational DFT analyses and the construction of a Hammett plot. Preliminary attempts at releasing phosphinated products from ruthenacycle complexes via protonolysis and phosphine substitution were conducted. An unexpected metallacyclic product of one of these attempts, [Ru(η5-indenyl)(κ2-CHCHPCy2)(PPh3)] (10), was identified and characterized.
Advisors/Committee Members: Rosenberg, Lisa (supervisor).
Subjects/Keywords: cycloaddition; metallacycles; ruthenium; P ligands; hydrophosphination
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Morrow, K. M. E. (2012). Phosphorus-containing ruthenacycles: exploring their potential in processes relevant to hydrophosphination. (Masters Thesis). University of Victoria. Retrieved from http://hdl.handle.net/1828/3890
Chicago Manual of Style (16th Edition):
Morrow, Krista Maria Elena. “Phosphorus-containing ruthenacycles: exploring their potential in processes relevant to hydrophosphination.” 2012. Masters Thesis, University of Victoria. Accessed May 06, 2021.
http://hdl.handle.net/1828/3890.
MLA Handbook (7th Edition):
Morrow, Krista Maria Elena. “Phosphorus-containing ruthenacycles: exploring their potential in processes relevant to hydrophosphination.” 2012. Web. 06 May 2021.
Vancouver:
Morrow KME. Phosphorus-containing ruthenacycles: exploring their potential in processes relevant to hydrophosphination. [Internet] [Masters thesis]. University of Victoria; 2012. [cited 2021 May 06].
Available from: http://hdl.handle.net/1828/3890.
Council of Science Editors:
Morrow KME. Phosphorus-containing ruthenacycles: exploring their potential in processes relevant to hydrophosphination. [Masters Thesis]. University of Victoria; 2012. Available from: http://hdl.handle.net/1828/3890
Princeton University
30.
Hoyt, Jordan.
Iron Catalyzed C-X (X = C, Si, B, H) Bond Forming Reactions
.
Degree: PhD, 2015, Princeton University
URL: http://arks.princeton.edu/ark:/88435/dsp0112579v570
► The synthesis of a new bis(imino)pyridine iron dinitogen compound, (iPr(tb)PDI)Fe(N2)2, was undertaken in order to explore the effect of restricting imine dissociation on catalysis. While…
(more)
▼ The synthesis of a new bis(imino)pyridine iron dinitogen compound, (iPr(tb)PDI)Fe(N2)2, was undertaken in order to explore the effect of restricting imine dissociation on catalysis. While this modification did not prevent the κ2-coordination of the ligand it did impart favorable solubility and crystallinity properties that were exploited in order to isolate and characterize catalytically relevant intermediates for intramolecular [2+2]
cycloaddition and hydrogenative cyclization reactions. In the case of the [2+2]
cycloaddition reactions changing the substrates allowed for the isolation and characterization of both the diene and metallacyclopentane intermediates. The diene compound was found to be best describe as high-spin iron(I) antiferromagnetically coupled to a mono reduced chelate resulting in the overall S=1 compound. The metallacycle was found to be best describe as intermediate-spin iron(III) antiferromagnetically coupled to a mono reduced chelate resulting in the overall S=1 compound. The catalytic cycle therefore occurs via an Fe(I)-Fe(III) redox event and the redox-active chelate remains mono reduced throughout this process.
The development of (tricPDI)Fe(N2)2 enabled expansion of the scope of intramolecular [2+2]
cycloaddition reactions to include 1,7-octadiene and derivatives. The use of (Me(iPr)PDI)Fe(N2)]2(μ2-N2) with these substrates led to divergent “Alder-Ene” reactivity yielding 1-methyl-2-methylenecyclohexane and the respective derivatives as a mixture of the possible regioisomers. Catalytically relevant metallacycles were isolated and characterized for both of these reactions. The scope of the [2+2] reaction was further expanded to include intermolecular variants. In the case of alkene dimerization reactions, trans-1,2-substituted cyclobutanes were observed as the exclusive product. When cross-cycloadditions between dienes and alkenes were run, cis-1,3-substituted cyclobutanes were obtained resulting from an iron alkyl-allyl intermediate distinct from the iron metallacyclopentanes.
The scope of alkene hydrosilylation and hydroboration with these catalysts were further explored to include substrates of interest for flavor and fragrance applications in collaboration with Firmenich. High-throughput screening techniques were applied toward the discovery of iron catalysts for the asymmetric hydrogenation of alkenes in collaboration with Merck. Poor conversions and selectivities were observed with a variety of bidentate phosphines and iron precursors. The reactivity of related, independently prepared complexes was explored.
Advisors/Committee Members: Chirik, Paul J (advisor).
Subjects/Keywords: Catalysis;
Cycloaddition;
Cycloisomerization;
Hydrogenation;
Hydrosilylation;
Iron
Record Details
Similar Records
Cite
Share »
Record Details
Similar Records
Cite
« Share
❌
APA ·
Chicago ·
MLA ·
Vancouver ·
CSE |
Export
to Zotero / EndNote / Reference
Manager
APA (6th Edition):
Hoyt, J. (2015). Iron Catalyzed C-X (X = C, Si, B, H) Bond Forming Reactions
. (Doctoral Dissertation). Princeton University. Retrieved from http://arks.princeton.edu/ark:/88435/dsp0112579v570
Chicago Manual of Style (16th Edition):
Hoyt, Jordan. “Iron Catalyzed C-X (X = C, Si, B, H) Bond Forming Reactions
.” 2015. Doctoral Dissertation, Princeton University. Accessed May 06, 2021.
http://arks.princeton.edu/ark:/88435/dsp0112579v570.
MLA Handbook (7th Edition):
Hoyt, Jordan. “Iron Catalyzed C-X (X = C, Si, B, H) Bond Forming Reactions
.” 2015. Web. 06 May 2021.
Vancouver:
Hoyt J. Iron Catalyzed C-X (X = C, Si, B, H) Bond Forming Reactions
. [Internet] [Doctoral dissertation]. Princeton University; 2015. [cited 2021 May 06].
Available from: http://arks.princeton.edu/ark:/88435/dsp0112579v570.
Council of Science Editors:
Hoyt J. Iron Catalyzed C-X (X = C, Si, B, H) Bond Forming Reactions
. [Doctoral Dissertation]. Princeton University; 2015. Available from: http://arks.princeton.edu/ark:/88435/dsp0112579v570
◁ [1] [2] [3] [4] [5] … [15] ▶
. 
Open Access Theses and Dissertations
