A SELECTIVE AND EFFICIENT METHOD FOR ALCOHOL OXIDATIONS MEDIATED BY N-OXOAMMONIUM SALTS IN COMBINATION WITH SODIUM BROMITE

被引：153

作者：

INOKUCHI, T ^{[1
]}

MATSUMOTO, S ^{[1
]}

NISHIYAMA, T ^{[1
]}

TORII, S ^{[1
]}

机构：

[1] OKAYAMA UNIV,FAC ENGN,DEPT APPL CHEM,OKAYAMA 700,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 02期

关键词：

D O I：

10.1021/jo00289a016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidation of primary and secondary alcohols leading to aldehydes, carboxylic acids, and ketones has been carried out in a N-oxoammonium salts-NaBrO2 system. Sodium bromite as a stoichiometric oxidizing reagent activates N-oxyl compounds (recycling catalysts) to their N-oxoammonium salts in a weakly basic medium, which oxidize primary hydroxyl groups preferentially rather than secondary ones to the corresponding aldehydes. Calcium hypochlorite is used as an alternative terminal oxidant in the same media. The procedure, applicable to the selective formation of ϒ- and 5-lactones, β-hydroxy aldehydes, and 2-acetoxy ketones, is advantageous in terms of reagent cost, safety, and ease of operation. © 1990, American Chemical Society. All rights reserved.

引用

页码：462 / 466

页数：5

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