O'brien E, Murphy M, Lynch D, Schaeffer M, Kissane M, Chopra J, Ford A, Ferguson G, Maguire AR;

2007

April

Organic and Biomolecular Chemistry

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

Validated

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5

8

1228

1241

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. 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.

10.1039/b618540a