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Vinylcopper(I) compounds: Part III: Direct conversion of 1-alkenylcuprates into stereospecifically substituted 1-halogeno-1-alkenes

1977; Royal Netherlands Chemical Society; Volume: 96; Issue: 6 Linguagem: Inglês

10.1002/recl.19770960607

1878-7096

H. Westmijze, J. Meijer, P. Vermeer,

Oxidative Organic Chemistry Reactions

Abstract Halogenation of vinylcopper(I) compounds [RR′CCHCu(Br or R)]MgX, prepared stereospecifically by cis ‐addition of [RCuBr]MgX or [R 2 Cu]MgX to 1‐alkynes R′‐C≡CH in tetrahydrofuran, with one of the halogenating reagents N ‐chlorosuccinimide, N ‐bromosuccinimide, BrCN, ICN or I 2 , leads in high yields to the corresponding 1‐halogeno‐1‐alkenes RR′CCHX (X = Cl, Br or I). The introduction of the halogen atom occurs with retention of configuration ( cis with respect to R).