Analytical Chemical Studies on Steroids. IV. The Zimmermann Reaction of 16- and 17-Oxosteroids

Abstract

The specificity of the Zimmermann reaction was examined with 38 kinds of 16- and 17-oxosteroids. The influences of environmental situation around oxo group on the reactivities were observed and interpreted in terms of stereochemistry. Of 16-substituted 17-oxosteroids only 16-monohalo derivative showed an exceptional behaviour giving a typical Zimmermann color. By treatment of the colored solution produced from 16α-bromodehydroisoandrosterone, the Zimmermann complex, 3β-hydroxy-16ξ-(2, 4-dinitrophenyl) androst-5-en-17-one, m.p. 186∼188°, was obtained and proved to be identical with that of dehydroisoandrosterone.