Peer-Reviewed Journal Details
Mandatory Fields
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: 22 ()
Optional Fields
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
Grant Details