Abstract
The reaction of nitrous acid with steroidal amides (I, VII, IX and X), α, β-unsturated ε-lactams (XIX and XXI), and enamine-type lactams (XXIV, XXVIII, XXX and XXXI) was studied. The amides mainly gave esters in low or modest yield with retention of the configuration. The α, β-unsaturated lactams gave N-nitroso-lactams quantitatively. The enamine-type δ-lactams gave oximino-δ-lactams in a high yield.