MEDIUM EFFECTS ON C,C-BOND CLEAVAGE IN THE ALCOHOL OXIDATION WITH CHROMIC-ACID

被引：14

作者：

MULLER, P

BLANC, J

机构：

[1] Département de Chimie Organique, Université de Genève, Genève

来源：

HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 06期

关键词：

D O I：

10.1002/hlca.19790620627

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The C,C‐bond cleavage which occurs during chromic acid oxidation of t‐butylphenylmethanol 1 and 1,2‐diphenylethanol 2 to the extent of up to 67% is reduced to 3% for 1 and 13% for 2 when the reaction is run in acetone, and totally suppressed upon co‐oxidation of the alcohols 1 and 2 with oxalic acid. Similarly, the yield of 7‐norbornanone obtained from 7‐norbornanol 7 is raised in going from acetic acid (24%) to acetone (41%) and approaches 100% in the co‐oxidation. With the co‐oxidation 5‐endo‐bicyclo [2.1.1]hexanol 3 is converted to the corresponding ketone in 54% yield. Mechanistic implications of these results are discussed. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：1980 / 1984

页数：5

共 42 条

[1]

BENSON D, 1976, MECHANISM OXIDATION, P152

[2] RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS [J].