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University of Saskatchewan

1. -6014-0932. Studies Towards the Synthesis of [10]-Annulenes.

Degree: 2017, University of Saskatchewan

This thesis begins with a historical perspective on aromaticity and benzene, including the discovery and proposed structures for benzene as well as proposed criteria for measuring aromaticity. The history of the synthesis and characterization of [10]-annulene is also discussed. Studies towards the synthesis of an aromatic all-cis-[10]-annulene derivative is covered in this dissertation. Two routes that were explored in efforts to obtain a chlorinated all-cis-[10]-annulene derivative, 40, are described. The primary route utilizes six chlorine atoms on the hydrocarbon skeleton (R=H) and uses a carbene [2+1] cycloaddition reaction as a key step to incorporate one of the two cyclopropane substituents (Scheme 1.0). The second cyclopropane unit is incorporated through a Diels-Alder reaction between diene 49 and tetrachlorocyclopropene 50, which also established the 10-carbon framework. The cleavage of the central olefin in the 10-carbon skeleton 51 is discussed, as well as difficulties encountered. In attempts to obtain the planar, aromatic [10]-annulene, efforts towards the elimination and oxidation reactions which lead to the aromatization of 55 are also presented. This thesis also discusses an alternative route that incorporates an additional chlorine atom on the carbon framework (R=Cl). The alternative route mirrors the previous pathway; one cyclopropane substituent is incorporated through a carbene [2+1] cycloaddition reaction, whereas the second unit is established via a Diels-Alder reaction (Scheme 1.0). Efforts towards cleaving the olefin in 51 to obtain the carbon skeleton 40 are also discussed. This work concludes with a general discussion and proposal for future directions, with an emphasis on alternative synthetic pathways. This study demonstrates the Diels-Alder reactions and ozonolysis of 51 is a viable strategy to form the functionalized skeleton required for [10]-annulene derivative 40. Advisors/Committee Members: Gravel, Michel (advisor), Hill, Bryan (committee member), Krol, Ed (committee member), Grosvenor, Andrew (committee member).

Subjects/Keywords: organic chemistry; [10]-annulene; aromaticity; organic synthesis

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APA (6th Edition):

-6014-0932. (2017). Studies Towards the Synthesis of [10]-Annulenes. (Thesis). University of Saskatchewan. Retrieved from http://hdl.handle.net/10388/8280

Note: this citation may be lacking information needed for this citation format:
Author name may be incomplete
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16th Edition):

-6014-0932. “Studies Towards the Synthesis of [10]-Annulenes.” 2017. Thesis, University of Saskatchewan. Accessed December 14, 2017. http://hdl.handle.net/10388/8280.

Note: this citation may be lacking information needed for this citation format:
Author name may be incomplete
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7th Edition):

-6014-0932. “Studies Towards the Synthesis of [10]-Annulenes.” 2017. Web. 14 Dec 2017.

Note: this citation may be lacking information needed for this citation format:
Author name may be incomplete

Vancouver:

-6014-0932. Studies Towards the Synthesis of [10]-Annulenes. [Internet] [Thesis]. University of Saskatchewan; 2017. [cited 2017 Dec 14]. Available from: http://hdl.handle.net/10388/8280.

Note: this citation may be lacking information needed for this citation format:
Author name may be incomplete
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

-6014-0932. Studies Towards the Synthesis of [10]-Annulenes. [Thesis]. University of Saskatchewan; 2017. Available from: http://hdl.handle.net/10388/8280

Note: this citation may be lacking information needed for this citation format:
Author name may be incomplete
Not specified: Masters Thesis or Doctoral Dissertation

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