Photochemistry of oximes. II. On the photo-induced formation of cycloalkanones and alkanoic acid amides from cycloalkanone oximes

Abstract

Cycloalkanone oximes were shown to give the corresponding alkanoic acid amides when irradiated in iso-propanol. α-Alkylated cyclohexanone oximes gave products corresponding to preferential cleavage on the side of the more substituted carbon atom. iso-Propanol was shown to transfer two hydrogen atoms specifically to the excited oxime molecule, acetone being formed in the process. In 1% aqueous solution, irradiation of oximes gave the corresponding ketones, ammonia, and oxygen.