Journal of Organic Chemistry p. 3378 - 3382 (1989)
Update date:2022-08-05
Topics:
Kwon, Byoung-Mog
Foote, Christopher S.
Khan, Saeed I.
Substituted trans-stilbenes react with singlet oxygen to give substituted diendoperoxides along with corresponding epoxides, cis-stilbenes, and benzaldehydes.The diendoperoxides rearrange readily to keto compounds on treatment with base.In methyl alcohol, solvent adducts are isolated.Monoendoperoxides are the primary products isolated from the photooxygenation of mono- and dimethoxystilbenes.Structures of several products were confirmed by NMR and X-ray crystallography.The results suggest that endoperoxide formation occurs via a polar intermediate such as a perepoxide or zwitterion.
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