Photochemical Reaction of N-Monosubstituted α-Oxoamides

Abstract

Photochemical synthesis of N-substituted 3-hydroxy-azetidin-2-ones from N, N-disubstituted α-oxoamides has been studied,¹ and recently, Aoyama et al have reported the mechanisms of these reactions.² However, to date, there have been no reports on the photochemical reaction of N-monosubstituted α-oxoamides. According to the mechanistic investigations on the photochemistry of N, N-disubstituted α-oxoamides² and the photochemical addition of 2-pyrrolidone to olefins under ultraviolet irradiation in the presence of acetone or benzophenone, which gives a mixture of 3-alkyl- and 5-alkyl-2-pyrrolidones (the 5-alkyl isomer always predominates)³, it seems possible that the N-monosubstituted α-oxoamide 1 might give the 3-hydroxyazetidin-2-one derivative 3 via the intermediate