Carbon-carbon bond fission on oxidation of primary alcohols to carboxylic acids

被引：8

作者：

Bekish, Andrei V. ^{[1
]}

机构：

[1] Belarusian State Univ, Dept Organ Chem, Minsk 220030, BELARUS

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 24期

关键词：

Alcohols; Carboxylic acids; Oxidation; Jones reagent; Bond fission; ACETYLENIC-COMPOUNDS; CHROMIC-ACID; ISOPROPYL-ALCOHOL; RESEARCHES; ALDEHYDES;

D O I：

10.1016/j.tetlet.2012.04.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Carbon-carbon bond cleavage is shown to be a general side reaction accompanying the oxidation of unbranched primary alcohols to the corresponding carboxylic acids using HNO3, CrO3/H2SO4/H2O/acetone, CrO3/CH3COOH, PDC/DMF, H5IO6/CrO3, KMnO4/W, KMnO4/HO-, NiCl2/NaClO, TEMPO/PhI(OAc)(2). Therefore, the product formed is always contaminated with a carboxylic acid containing one carbon atom less. Systems such as PhI(OAc)(2)/TEMPO or H5IO6/CrO3/CH3CN reduce to a minimum the content of this impurity. Temperature, the order of reagent addition, and additives such as oxalic acid or cerium salts produce a profound effect on the formation of the undesirable impurity during the Jones oxidation of primary alcohols. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3082 / 3085

页数：4

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