ALPHA-PHOSPHORYL SULFOXIDES .10. A GENERAL-SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-CHLOROVINYL SULFOXIDES

A general and efficient synthesis of enantiomeric alpha-chlorovinyl p- tolyl sulfoxides 1 using S)(S)-alpha-chloro-alpha-dimethoxyphosphorylm ethyl p-tolyl sulfoxide as a key substrate for the Horner-Wittig react ion with carbonyl compounds is described. The E/Z ratio of geometrical isomers of 1 was determined and briefly investigated. The X-ray diffr action structures of (Z)-1-chloro-1-p-tolylsulfinyl-2-phenyl-ethene an d Z)-1-chloro-1-p-tolylsulfinyl-2-(2-thienyl)-ethene are reported. Cop yright (C) 1996 Elsevier Science Ltd.