Stereoselective cyanation of vinyl halides catalyzed by tetracyanocobaltate (I)

T Funabiki, H Hosomi, S Yoshida…

Index: Funabiki, Takuzo; Hosomi, Hiroaki; Yoshida, Satohiro; Tarama, Kimio Journal of the American Chemical Society, 1982 , vol. 104, # 6 p. 1560 - 1568

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Citation Number: 38

Abstract

Abstract: Tetracyanocobaltate (I),[Co (CN), 13, which is formed in an aqueous alkaline solution under a hydrogen atmosphere, catalyzes the cyanation of vinyl halides to form 2- alkenenitriles, The reaction is stereoselective, forming nitriles with retention of configuration, except for (Z)-2-bromobut-2-ene, which forms a mixture of nearly equimolar isomeric nitriles. Reactivity is dependent on the CN: Co ratio and is highest when the ratio is slightly lower ...