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Date of Award

2016

Document Type

Restricted Thesis: Campus only access

Degree Name

Bachelor of Science

Department

Chemistry

First Advisor

Dr. C. Wade Downey

Abstract

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) serves as an effective catalyst by activating substrates for nucleophilic attack. When reacted with stoichiometric amounts of TMSOTf, N- phenyl nitrones react readily with zinc acetylides, and deprotection of the product with aqueous acid yields the N-hydroxyl propargylamine. Zinc acetylides form easily from terminal alkynes in the presence of i-Pr2NEt and 20 mol% ZnBr2. Generally high yields are observed for reactions of these acetylides with nitrones derived from aromatic aldehydes. Trimethylsilyl trifluoromethanesulfonate generates propargyl cations from propargyl alcohols and propargyl carboxylates. In the presence of an amine base, a ketone nucleophile can be converted to the enol silane, which subsequently attacks the propargyl cation generated by the TMSOTf. In addition to ketones, triethylsilane and thiols have been shown to be effective nucleophiles for this substrate.

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