Nucleophilic Addition-Elimination Reactions of N-(p-Tolylsulphonyl)vinylsulphoximines: Preparation of α-Methylene Nitriles and Phosphonates

Article abstract of DOI:10.1016/0040-4039(91)80705-B

Treatment of N-(p-tolylsulphonyl)vinylsulphoximines (1) with lithium cyanide in DMF at room temperature leads to efficient formation of α,β-unsaturated nitriles (3), via a Michael addition-proton transfer-elimination process, in which the polarity of the double bond is reversed.Analogous reaction with lithium dimethylphosphonate leads to β-dimethylphosphonyl sulphoximines (7), which are converted to α,β-unsaturated phosphonates (6) by treatment with NaOMe.