Synthesis of mono- and disubstituted sulfines via β-elimination of chloroform from trichloromethyl sulfoxides

Article abstract of DOI:10.1016/S0040-4020(97)00904-6

A new method for the synthesis of thioaldehyde and thioketone S-oxides by an unusual base-induced β-elimination of chloroform from readily available allylic and benzylic trichloromethyl sulfoxides is described. The reaction proceeds smoothly under mild conditions. The facile preparation of α,β-unsaturated sulfines by the new method is of special interest. A possible mechanism for this remarkable sulfine synthesis and apparently unprecedented β-elimination of chloroform is presented.