α-Halo carbanion intermediates: I. Synthesis of α-chlorobibenzyls and stilbenes via the α-metalation of benzyl chlorides with n-butyllithium

DF Hoeg, DI Lusk

Index: Hoeg,D.F.; Lusk,D.I. Journal of Organometallic Chemistry, 1966 , vol. 5, p. 1 - 12

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Abstract

Abstract The reactions of variously substituted benzyl chlorides with n-butyllithium in tetrahydrofuran at low temperatures (− 100) leads to the formation of the correspondingly substituted α-chlorobibenzyl (1, 2-diarylchloroethane) in good-to-excellent yields. The corresponding symmetrically substituted stilbenes are readily formed in good yields by thermal dehydrochlorination of the α-chlorobibenzyl.