Off-campus University of Richmond users: To download campus access theses, please use the following link to log in to our proxy server with your university username and password.

Date of Award

2019

Document Type

Restricted Thesis: Campus only access

Degree Name

Bachelor of Science

Department

Chemistry

Abstract

Ketones undergo in situ enol silane formation in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and an amine base, and subsequently undergo alkylation with propargyl or allyl carboxylates ionized by residual TMSOTf to generate []-alkynyl ketones or []-unsaturated ketones, respectively. Such reactions proceed due to the ability of TMSOTf to act as both a silylating agent and a Lewis acid. The propargyl or allyl carboxylates react efficiently with aryl-alkyl and alkyl-alky ketones, as well as thioesters. Both aryl and alkyl substitution is tolerated on the propargyl carboxylate at the 3-position, and the 1-position may be substituted by various aryl groups. Similarly, aryl substitution is tolerated at both positions on the allyl carboxylates.

Share

COinS