Date of Award
Bachelor of Science
Biochemistry & Molecular Biol.
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.
Hussein, Mohamad Ahmad, "An in Situ One Pot N-allylation and Friedel–Crafts Alkylation of diaryl substituted allyl propionates mediated by Trimethylsilyl Trifluoromethanesulfonate" (2023). Honors Theses. 1702.
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