Reactions of Ketenethioacetal Derivatives with Sodium Cyanide and Reactions of These Products with Nucleophilic Reagents

Abstract

Sodium cyanide was reacted with 2-cyano-3, 3-bis(methylthio)acrylonitrile (Ia) and methyl 2-cyano-3, 3-bis(methylthio)acrylate (Ib), the derivatives of ketenethioacetal, and 2, 3-dicyano-3-methylthioacrylonitrile (IIa), and cis and trans compounds of methyl 2, 3-dicyano-3-(methylthio)acrylate (IIb, c) were obtained. Reaction of these compounds (IIa, b, c) with nucleophilic reagents (amines and active methylenes) gave the corresponding compounds in which methylthio group had been substituted, in a good yield.