Reaction of 1-chloro-2-alkylcycloalkenes with organolithium reagents. A novel cyclopropanation reaction involving the generation of carbenes from vinyl halides

PG Gassman, JJ Valcho, GS Proehl…

Index: Gassman,P.G.; Valcho,J.J.; Proehl,G.S. Journal of the American Chemical Society, 1980 , vol. 102, p. 6519

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Citation Number: 31

Abstract

Abstract: The reactions of 1-chloro-2-alkylcycloalkenes with organolithium reagents have been investigated in detail. It has been demonstrated that six-, seven-, and eight-membered cyclic olefins yield bicyclo [4.1. O] heptanes, bicyclo [5.1. O] octanes, and bicyclo [6.1. O] nonanes, respectively. The mechanism of this transformation has been examined in detail and has been shown to involve a multistep process which includes (a) extraction of the ...