Journal of the American Chemical Society

Carbenes from Alkyl Halides and Organolithium Compounds. V. Formation of Alkylcyclopropenes by Ring Closure of Alkenyl Substituted Carbenoid Intermediates

GL Closs, LE Closs

Index: Closs,G.L.; Closs,L.E. Journal of the American Chemical Society, 1963 , vol. 85, p. 99 - 104

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Citation Number: 52

Abstract

Reactions of 1, 2-dimethylpropenyllithium and 2-methylpropenyllithium with methylene chloride give 1, 3, 3-trimethylcyclopropene and 3, 3-dimethylcyclopropene, respectively. Product formation is conveniently accounted for in terms of a mechanism invoking alkenyl substituted intermediates. This hypothesis is strengthened by the observation that a- dehydrochlorination on l-chloro-2, 3-dimethyl-2-butene and a-debromination on 1, l- ...