SINGLET OXYGEN AND TRIAZOLINEDIONE ADDITION TO AZINES

Article abstract of DOI:10.1016/S0040-4020(01)82076-7

Photooxygenation of azines, i.e., adamantanone azine (1) and benzonorborn-7-one azine (4), afforded in addition to the corresponding ketones, lactones derived from a carbonyl oxide intermediate via an electron transfer pathway.On the other hand, 4-substitued-1,2,4-triazoline-3,5-diones (TAD) react with azine 1 to give a 1,3-dipole, an azomethinimine intermediate as nitrogen analogue of a carbonyl oxide, which afforded the <2+3>-cycloadducts in treatment with dipolarophiles.The mechanistic implications are discussed.