Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO

被引：144

作者：

Manna, Srimanta ^{[1
]}

Jana, Sandipan ^{[1
]}

Saboo, Tapish ^{[1
]}

Maji, Arun ^{[1
]}

Maiti, Debabrata ^{[1
]}

机构：

[1] Indian Inst Technol Bombay Powai, Dept Chem, Bombay 400076, Maharashtra, India

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 46期

关键词：

OLEFINS; NITROSTYRENES; HYDROGENATION; NITROALKENES; DERIVATIVES; CONVENIENT; CATALYSTS; ADDITIONS; STYRENES; ACIDS;

D O I：

10.1039/c3cc41576g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nitroolefins are usually synthesized using the Henry reaction. Here we report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from alpha,beta-unsaturated carboxylic acids using t-butylnitrite (t-BuONO) and TEMPO. alpha,beta-Unsaturated carboxylic acids bearing beta-aromatic and beta-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.

引用

页码：5286 / 5288

页数：3

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