Oxidation of Indoles by Singlet Oxygen and Dimethyldioxirane: Isolation of Indole Dioxetanes and Epoxides by Stabilization through Nitrogen Acylation

Article abstract of DOI:10.1016/S0040-4039(00)73964-5

Stabilization through N-acylation allowed the isolation of the labile indole dioxetanes 2, which were transformed by dimethyl sulfide deoxygenation to the corresponding indole epoxides 5; the latter were also independently prepared by dimethyldioxirane oxidation.Key words: Indoles, carbazoles, dimethyldioxirane, singlet oxygen, dioxetanes, epoxides