Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of alpha-thioamides to alpha-thio-beta-chloroacrylamides.

Treatment of a series of alpha-thioamides with N-chlorosuccinimide results in efficient transformation to the analogous alpha-thio-beta-chloroacrylamides. The mechanistic pathway has been established through isolation and characterisation of intermediate compounds. The scope of the transformation has been explored-aryl and alkylthio substituents, primary, secondary and tertiary amides can be employed.