Steroids. Part 21. Photorearrangement of steroidal nitronate salts and a N-butyl spiro-oxaziridine

Abstract

Irradiation, at 254 nm, of ethanol solutions of nitro-steroids in the presence of an excess of sodium ethoxide gave a range of products including hydroxamic acids, ketones, and alkenes possibly derived from the anions of the N-hydroxyoxaziridines. Alternatively, the ketones and hydroxamic acids may be derived from the anions of the hydroxy-nitroso compounds. The proportions of products depend on the ring size and stereochemistry and the photoreactions differ significantly from those observed for N-alkyl spiro-oxaziridines including a steroidal N-butyl spiro-oxaziridine.