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

2007

January

Organic & Biomolecular Chemistry

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

Validated

WOS: 23 ()

FRIEDEL-CRAFTS REACTION ORGANIC-SYNTHESIS LACTAMS CHLOROSULFIDES SOLVENTS AMIDES

5

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.

CAMBRIDGE

1477-0520

10.1039/b618540a