Reaction of 1O2 with strained olefins. 3. Photooxidation of vinylcyclopropanes

A Frimer, D Roth

Index: Frimer,A.A.; Roth,D. Journal of Organic Chemistry, 1979 , vol. 44, # 22 p. 3882 - 3887

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Citation Number: 16

Abstract

The reaction of '02 with 1, l-dicyclopropylpropene (13) and its 2-methyl analogue (12) yields two “ene” products corresponding to the abstraction of an allylic hydrogen from either the methyl or the cyclopropyl group. In the latter case an alkylidenecyclopropane is formed despite a resulting 11.4 kcal/mol increase in strain energy. This indicates that* 02 is insensitive to any strain that might develop in the final product. In contradistinction, 2- ...