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Rutgers University

1. Zhang, Yue, 1976-. Formation and reactivity of allenes and spirodiepoxides.

Degree: PhD, Chemistry and Chemical Biology, 2010, Rutgers University

Disclosed are the studies on allene and functionalized medium sized ring synthesis as well as applications of spirodiepoxide based methods. A new method of making allenes via C-C bond fragmentation was developed by which, most notably, an enantioenriched functionalized cyclic allene was synthesized. Mechanistic studies provide a framework for understanding this reaction in relation to other known modes of fragmentation. The synthesis of a chiral cyclononadienone was completed. This product has been shown to be a key intermediate towards many members of the xenicane family. Three epoxomicin analogues were synthesized. The issue of selectivity in allene oxidation was addressed in the course of this study. A model study towards erythronolide A was completed in which the feasibility of selective double cuprate addition to a bis[spirodiepoxide] macrolactone controlled by the macrocyclic environment was demonstrated. Lastly, the development of new reactions using spirodiepoxides to directly access densely functionalized structures in single- or two-flask procedures is reported.

Advisors/Committee Members: Zhang, Yue, 1976- (author), Williams, Lawrence J (chair), Knapp, Spencer (internal member), Warmuth, Ralf (internal member), Hu, Longqin (outside member).

Subjects/Keywords: Allene – Oxidation; Allene – Reactivity

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APA (6th Edition):

Zhang, Yue, 1. (2010). Formation and reactivity of allenes and spirodiepoxides. (Doctoral Dissertation). Rutgers University. Retrieved from http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056874

Chicago Manual of Style (16th Edition):

Zhang, Yue, 1976-. “Formation and reactivity of allenes and spirodiepoxides.” 2010. Doctoral Dissertation, Rutgers University. Accessed September 23, 2019. http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056874.

MLA Handbook (7th Edition):

Zhang, Yue, 1976-. “Formation and reactivity of allenes and spirodiepoxides.” 2010. Web. 23 Sep 2019.

Vancouver:

Zhang, Yue 1. Formation and reactivity of allenes and spirodiepoxides. [Internet] [Doctoral dissertation]. Rutgers University; 2010. [cited 2019 Sep 23]. Available from: http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056874.

Council of Science Editors:

Zhang, Yue 1. Formation and reactivity of allenes and spirodiepoxides. [Doctoral Dissertation]. Rutgers University; 2010. Available from: http://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056874

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