학술논문
N-benzyl- N-[( E)-2-phenylethenyl]trifluoromethanesulfonamide.
Document Type
Article
Author
Source
Subject
*AMINE synthesis
*BROMINATION
*DEBROMINATION
*BENZYL compounds
*METHYL triflate
*BENZYL alcohol synthesis
*HYDROGENATION
*CHEMICAL reactions
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Language
ISSN
1070-4280
Abstract
In the search for an approach to N-vinyltriflamides with a free NH group TfNHCH=CHR (Tf = CFSO) N-(benzyl)- N-(2-bromo-2-phenylethenyl)triflamide TfN(Bn)CH=CHPh was synthesized through bromination-dehydrobromination of N-(benzyl)- N-(2-phenylethyl)triflamide. At removing the benzyl protecttion by the action of trifluoromethanesulfonic acid benzyl alcohol separated; however instead of the target N-styryltriflamide unexpectedly the product of its hydrogenation was obtained, N-(2-phenylethyl)triflamide. Obviously, the benzyl alcohol was the hydrogen donor, and the easy hydrogenation was facilitated by the high electrophilicity of the double bond in N-styryltriflamide because of strong electron-acceptor effect of the triflyl group. [ABSTRACT FROM AUTHOR]