Photochemistry of Aliphatic Imides. Synthesis of Azetidine-2,4-diones via Photochemical Isomerization of Succinimides and N-Formyl-N-methyl α, β -Unsaturated Amides

Article abstract of DOI:10.1021/jo00314a006

Photochemical reactions of alkyl-substituted succinimides and N-formyl-N-methyl α, β -unsaturated amides were studied.Photolysis of succinimide 1 gave azetidine-2,4-dione 2 together with a small amount of 3.The photoinduced ring-contraction reaction is explained in terms of a two-photon mechanism.Similarly, several other succinimide derivates photochemically gave the corresponding azetidine-2,4-diones.In addition, the photochemical cyclization of 3 to 2 was extended to the synthesis of azetidine-2,4-diones from N-formyl-N-methyl α, β -unsaturated amides.