STEREOCHEMICAL ASPECTS OF THE VANADIUM-CATALYZED EPOXIDATION OF CONFORMATIONALLY BIASED CYCLOHEX-2-EN-1-OLS BY ALKYL HYDROPEROXIDES

被引：30

作者：

DEHNEL, RB ^{[1
]}

WHITHAM, GH ^{[1
]}

机构：

[1] DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 04期

关键词：

D O I：

10.1039/p19790000953

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the vanadium-catalysed epoxidation of cis- and trans-5-t-butylcyclohex- 2-enol the trans-(pseudoaxial) alcohol is epoxidised ca. 34 times faster than the cis-isomer. A significant competing process is oxidation to αβ-unsaturated ketone, and this becomes the predominant reaction in the case of the cis-alcohol.

引用

页码：953 / 955

页数：3

共 9 条

[1]

BERNSTEIN SH, 1967, J AM CHEM SOC, V89, P4722

[2] EPOXIDATION OF ALLYLIC ALCOHOLS WITH PEROXY-ACIDS - ATTEMPTS TO DEFINE TRANSITION STATE GEOMETRY [J].