Chemistry of Singlet Oxygen. 52. Reaction with trans-Stilbene

Article abstract of DOI:10.1021/jo00275a024

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.