Spectroscopic studies of the electrophilic activation of amides with triflic anhydride and pyridine

被引：135

作者：

Charette, AB ^{[1
]}

Grenon, M ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2001年 / 79卷 / 11期

关键词：

amides; triflic anhydride; pyridinium intermediates; NMR study;

D O I：

10.1139/cjc-79-11-1694

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of amides with trifluoromethanesulfonic (triflic) anhydride in the presence of pyridine was thoroughly investigated by NMR spectroscopic techniques. Different pyridinium intermediates were generated from secondary amides, tertiary amides with enolizable protons, and tertiary amides lacking enolizable protons. It was found that the actual triflating reagent is N-(trifluoromethylsulfonyl)pyridinium triflate 11 which is formed by the initial reaction of triflic anhydride with pyridine. The alcoholysis of these intermediates yields O-alkyliminium ethers which can then be easily hydrolyzed under mild acidic conditions to the corresponding esters.

引用

页码：1694 / 1703

页数：10

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