1,2-Dioxetane Formation in Photooxygenation of N-Acylated Indole Derivatives

Article abstract of DOI:10.1021/jo00072a042

Eight N-acylated indole derivatives (1a-h) react with singlet oxygen at low temperature (-5 to -78 deg C) in methanol-d₄ or methanol-d₄ - methylene chloride-d₄ to afford 1,2-dioxetanes 2a-h, whose structures are characterized by low-tempearture 13C NMR and 1H NMR spectra and chemical transformations.These strained 1,2-dioxetanes decompose smoothly and exclusively to dicarbonyl cleavage products 3a-h upon warming to room temperature.