STEREOCHEMISTRY OF 1-HYDROXYCYCLOHEXANECARBOXYLIC ACIDS OBTAINED BY HYDROLYSIS OF CYANOHYDRINS OF SOME METHYLCYCLOHEXANONES

被引：12

作者：

HARNDEN, MR

机构：

[1] Organic Chemistry Department, Research Division, Abbott Laboratories, North Chicago

来源：

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 06期

关键词：

D O I：

10.1039/j39690000960

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrolysis of the total cyanohydrin product obtained from several 3.5-methyl-substituted cyclohexanones yielded in each case only the hydroxy-acid with an equatorial carboxy-group. Oxidation of the mixture of ethynyl carbinols prepared from cis-3,5-dimethylcyclohexanone yielded predominantly the hydroxy-acid with an axial carboxy-group. Configurational assignments are based upon measurements of the dissociation constants and n.m.r. spectra of the hydroxy-acids and their O-acetyl derivatives. Both steric and kinetic arguments are presented to rationalize these results.

引用

页码：960 / &

共 14 条

[1]

AHLQUIST L, 1959, ARK KEMI, V14, P171

[2]

AKHREM AA, 1967, ZH ORG KHIM, V3, P57

[3] OXYGEN EXCHANGE AS EVIDENCE FOR THE EXISTENCE OF AN INTERMEDIATE IN ESTER HYDROLYSIS [J].