Date of Award


Document Type


Degree Name

Bachelor of Science


Biochemistry & Molecular Biol.

First Advisor

C. Wade Downey


When propargyl or allyl propionates are treated with trimethylsilyl trifluoromethanesulfonate, ionization occurs. In situ formation of silyl imidates from secondary or primary amides provides the nucleophile, which may attack the allyl cation to yield the N-substituted amide. When Nphenyl amides are employed, Friedel–Crafts alkylation at the para position competes with Nalkylation. Yields are high for the N-alkylated products and can be modified to favor the Friedel– Crafts product for amides with phenyl-substituted nitrogens.

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