Aspects of stereochemistry. Part XX. The formation of 5-cyano-3-ketones from 3-oxo-Δ4-steroids
Abstract
Reaction of 3-oxo-Δ4-steroids with calcium cyanide in N-methylpyrrolidone gives 5α- and 5β-cyano-3-oxo-steroids. The isomer ratio is close to 1 : 1 for androstenone, cholestenone and testosterone, and about 3 : 5 (α:β 5-cyanide) for progesterone.