Tetrahedron Letters p. 3119 - 3122 (1991)
Update date:2022-08-04
Topics:
Bailey, Peter L.
Jackson, Richard F. W.
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.
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