Studies in sulphoxide chemistry

The effect of further stabilisation on the generation of sulphoxide carbanions, under milder conditions than those commonly employed by the generation of dimethylsulphoxide carbanion, has been briefly investigated. Both dibenzyl sulphoxide and diphenylsulphinylmethane failed to react sufficiently under milder conditions. Attempts to secure the Michael addition of DMSO- to a wide variety of conjugated systems has proved successful in most cases. Thus a wide variety of α-phenylcinnamonitriles, formed by condensation of benzyl cyanide with substituted benzaldehydes, has given DMSO adducts in good yield. These adducts have shown interesting features in their mass spectral breakdown patterns explicable in terms of Hammett coefficients. [Continues.]