Reactions of androsta-3,5-dienes with m-chloroperbenzoic acid

Abstract

The reaction of androsta-3,5-diene and of androsta-3,5-dien-17-one with one or 2 molar equiv. of m-chloroperbenzoic acid give complex mixtures of products. Only low yields of diepoxides are formed using 2 equiv. of peracid in ether as solvent, unsaturated vic-3,4-diols being the major products. Use of 1 equiv. of peracid leads, inter alia, to unsaturated hydroxy-m-chlorobenzoates. The formation of these and other products are discussed.