Cyclopropanes. XXX. Reductive cleavage of cyclopropane rings

HM Walborsky, MS Aronoff…

Index: Walborsky,H.M. et al. Journal of Organic Chemistry, 1971 , vol. 36, # 8 p. 1036 - 1040

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Citation Number: 10

Abstract

l, l-Biphenylene-2-methylcyclopropane (5) was synthesized and subjected to reductive cleavage with sodium and lithium in liquid ammonia, sodium in glyme, sodium naphthalide in glyme, and by controlled potential electrolysis in acetonitrile at a mercury cathode. The reductive cleavage of 5 yielded under all conditions a mixture of 9-propylfluorene (6) and 9- isopropylfluorene (7) with the isomer ratio of 6: 7 varying from 96: 4 to 81: 19. The ...