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Date of Award
4-30-2021
Document Type
Restricted Thesis: Campus only access
Degree Name
Bachelor of Science
Department
Biochemistry & Molecular Biol.
First Advisor
Dr. C. Wade Downey
Abstract
Allyl propionates are readily ionized by trimethylsilyl trifluoromethanesulfonate to provide allyl carbocations. In the same reaction mixture, ketones can be transformed into enol silanes if an amine base is present. With the formation of carbocations and enol silane in one pot, an SN1 reaction occurs to yield the g,d-unsaturated ketone products. Selectivity for unsymmetrical allyl carbocations is influenced by electronic effects induced by substituents on the enol silane and the carbocation.
Recommended Citation
Zhong, Hanyu, "Direct Allylation of Ketones with Trimethylsilyl Trifluoromethanesulfonate and Triethylamine" (2021). Honors Theses. 1536.
https://scholarship.richmond.edu/honors-theses/1536