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Communication | Special issue | Vol 11, No. 1, 1978, pp.323-326
Published online, 1st January, 1970
DOI: 10.3987/S(N)-1978-01-0323
Low-temperature Characterization of a Dioxetane Produced in the Sensitized Photooxygenation of a Vinylcyclopropane, 3,10-Dispirocyclopropyltricyclo [,6] deca-4,8-diene

Hitoshi Takeshita,* Toshihide Hatsui, and Hiroaki Mametsuka

*Instituete of Advanced Material Study, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


The sensitized photooxidation of the title olefin at -80 °C was, contrary to the results of the reaction at room temperature, shown to afford only the dioxetane and its cleavage product, regardless of the sensitizers and the solvent used. Low-temperature characterization of the product by means of 1H- and 13C-NMR as well as some chemical transformations confirmed the occurrence of the (2+2) π-cycloaddition mode in the singlet oxygen oxidation of vinylcyclopropanes.