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Reaction of 1-halo-1-organothio or 1-halo-1-organoseleno alkenes with CuCN in NMP as solvent provides a-phenylthio or a-phenylseleno acrylonitriles in good yields. The reaction showed a low stereoselectivity and the products were obtained as E/Z mixtures of isomers.

Synthesis of organothioacrylonitriles and organoselenoacrylonitriles by reaction of 1-Halo-1-chalcogenoalkenes with CuCN