The Journal of Organic Chemistry

Chemistry of singlet oxygen. 53. Environmental effects on the photooxygenation of 2-methoxy-3-methyl-2-cyclopenten-1-one

BM Kwon, CS Foote

Index: Kwon, Byoung-Mog; Foote, Christopher S. Journal of Organic Chemistry, 1989 , vol. 54, # 16 p. 3878 - 3882

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Citation Number: 21

Abstract

Photooxygenation of 2-methoxy-3-methyl-2-cyclopenten-l-one (1) gives both ene and dioxetane products. The product distribution depends on temperature and solvent. In CD30D, the photooxygenation of 1 gives solvent adducts as initial products, and the ratio of stereoisomers is very sensitive to the amount of CD, OD in the reaction mixture. The results are discussed in terms of possible intermediates for the ene and dioxetane products, ...