Extending the haloform reaction to non-methyl ketones: Oxidative cleavage of cycloalkanones to dicarboxylic acids using sodium hypochlorite under phase transfer catalysis conditions

被引：13

作者：

Rothenberg, G ^{[1
]}

Sasson, Y ^{[1
]}

机构：

[1] HEBREW UNIV JERUSALEM,CASALI INST APPL CHEM,IL-91904 JERUSALEM,ISRAEL

来源：

TETRAHEDRON | 1996年 / 52卷 / 43期

关键词：

D O I：

10.1016/0040-4020(96)00816-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclohexanone is readily oxidized to adipic, alpha,alpha - dichloroadipic, glutaric and succinic acids by sodium hypochlorite under phase transfer conditions. The selectivity is highly dependent on the pH of the reacting system. A consecutive chlorination-hydrolysis mechanism is proposed in which only cyclohexanone is a reactive substrate leading in parallel to the melange of oxidized products. Cyclooctanone and cyclopentanone are similarly oxidized. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：13641 / 13648

页数：8