516. Steroids and Walden inversion. Part LI. The solvolysis of 4, 4-dimethylcholest-5-en-3α-yl toluene-p-sulphonate

CW Shoppee, GAR Johnston

Index: Shoppee,C.W.; Johnston,G.A.R. Journal of the Chemical Society, 1962 , p. 2684 - 2691

Full Text: HTML

Citation Number: 4

Abstract

Solvolysis of 4, 4-dimethylcholest-5-en-3a-yl toluene-p-sulphonate gives the corresponding 3or-alcohol (10%)[or acetate (5x1, 3p, 4P-dimethylcholest-5-en-4cc-01 (5%), and 3, 4- dimethylcholesta-3, 5-diene (85%). The reaction is not synartetically accelerated, and is regarded as proceeding through a classical carbonium ion, which rapidly gives a non- classical bridged cation of greater thermodynamic stability.