Treatment of a series of α-thioamides with N-chlorosuccinimide results in efficient transformation to the analogous α-thio-β- 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. In most instances, the chloroacrylamides are formed exclusively as the Z-stereoisomer; however, with tertiary propanamides or with amides derived from butanoic or pentanoic acid a mixture of E- and Z-stereoisomers is formed. © The Royal Society of Chemistry.
Murphy, M., Lynch, D., Schaeffer, M., Kissane, M., Chopra, J., O’Brien, E., … Maguire, A. R. (2007). Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β- chloroacrylamides. Organic and Biomolecular Chemistry, 5(8), 1228–1241. https://doi.org/10.1039/b618540a