Hydroxy-steroids. Part XV. A quantitative study of the epoxidation of 3-substituted cholest-5-enes

Abstract

Examination of the conversion of 3-substituted cholest-5-enes into 5α,6β- and 5β,6β-epoxides by various peroxyacid–solvent combinations gives values for the ratios of isomers produced and the rate constants of the reactions. Peroxylauric acid in benzene forms a high proportion of the α-epoxide (e.g. 85% from cholesteryl 3,5-dinitrobenzoate); the use of p-nitroperoxybenzoic acid in chloroform leads to fast epoxidation.