The Journal of Organic Chemistry

Spontaneous oxygenation of cyclic olefins. Effects of strain

PD Bartlett, R Banavali

Index: Bartlett, Paul D.; Banavali, Rajiv Journal of Organic Chemistry, 1991 , vol. 56, # 21 p. 6043 - 6050

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Citation Number: 33

Abstract

Reactivity of strained olefins 1-3, 41, and 44 toward spontaneous oxygenation has been evaluated. Anglestrained olefins 1, 32, and 35 react spontaneously with ground-state triplet oxygen, at room temperature, to yield quantitatively, not copolymers or hydroperoxides, but epoxides and diketones in approximately a 2: l ratio. The autoxidation of 1 is carried out with various solvents, inhibitors, initiators, and in the presence of 2 and 1, 2- ...