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Date of Award
2014
Document Type
Restricted Thesis: Campus only access
Degree Name
Bachelor of Science
Department
Chemistry
First Advisor
Dr. Kristine A. Nolin
Abstract
The homologous conjugate addition of heteroaromatic compounds to electron deficient cyclopropanes was facilitated by calcium triflimide. The reactivity of benzofuran and 1- methylindole with a variety of differentially substituted cyclopropanes was explored and the product yields of the reactions were determined. The reaction was optimized by varying temperatures, solvents, nucleophile equivalents, calcium catalysts and co-catalysts, and catalyst loading. The optimal reaction conditions of the homologous conjugate addition were identified and yields for addition to a variety of cyclopropane substrates were obtained. Yields for the addition of benzofuran were moderate and varied from a high of 77% to a low of 28% for differentially substituted cyclopropanes. Addition of 1-methylindole proceeded in good to excellent yield, 87-99 %. The difference in yield for the two nucleophiles was significant and possible explanations for the low benzofuran yields were explored. The final products were characterized by NMR data and a potential mechanism has been proposed. The project has identified a calcium (II) complex as a robust catalyst for C–C bond for ing reactions, thus forwarding the effort to find methods that are more environmentally benign.
Recommended Citation
Murphy, Kristen L., "The homologous conjugate addition of heteroaromatic compounds to donor-acceptor cyclopropanes" (2014). Honors Theses. 907.
https://scholarship.richmond.edu/honors-theses/907