Tetrahedron p. 5273 - 5280 (1986)
Update date:2022-08-05
Topics:
Sato, Rikiya
Sonobe, Hideki
Akasaka, Takeshi
Ando, Wataru
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.
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