N-benzyl-N-[(E)-2-phenylethenyl]trifluoromethanesulfonamide

被引：0
|
作者：
B. A. Shainyan
I. V. Ushakova
机构：
[1] Russian Academy of Sciences,Favorsky Irkutsk Institute of Chemistry, Siberian Branch
来源：
Russian Journal of Organic Chemistry | 2014年 / 50卷
关键词：
Benzyl; Benzyl Alcohol; Benzyl Bromide; Trifluoromethanesulfonamide; BnOH;
D O I：
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中图分类号：
学科分类号：
摘要：
In the search for an approach to N-vinyltriflamides with a free NH group TfNHCH=CHR (Tf = CF3SO2) 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.
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页码：1093 / 1096
页数：3
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