Une nouvelle reaction de photooxydation: transformation de lactames et d'amides en imides et hydroperoxydes

Irradiation of an oxygen-saturated solution of N-methyl 2-pyrrolidone in t-BuOH leads to N-methylsuccinimide. This reaction can be applied to other lactams and amides (2,3,12–16) and gives the corresponding imide. Lactams 27, 28 and 31 which are substituted α to the nitrogen atom give α hydroperoxy or α hydroxyamides 29, 30 and 32. The benzophenone triplet regioselectively abstracts the hydrogen atom α to the amide nitrogen to give radicals which are then oxidized. The decomposition mechanism of the peroxy radicals is discussed.