Oxidation of N-acylindoles by dimethyldioxirane and singlet oxygen: substituent effects on thermally persistent indole epoxides and dioxetanes

…, K Peters, B Schmiedeskamp

文献索引：Adam, Waldemar; Ahrweiler, Michael; Peters, Karl; Schmiedeskamp, Bernd Journal of Organic Chemistry, 1994 , vol. 59, # 10 p. 2733 - 2739

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被引用次数: 49

摘要

Photooxygenation of the N-acylindoles la-d afforded the labile indole dioxetanes 2 and the relatively stable allylic hydroperoxides 3. The dioxetanes 2a, c, d were sufficiently stable for isolation and spectral characterization. Additionally, they were characterized by chemical transformations, namely reduction to the indole epoxides 5 by dimethyl sulfide, acid- catalyzed rearrangement to allylic hydroperoxides 3c, d, and thermolysis to the cleavage ...