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. 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.
Murphy
Maureen
M
Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland.
Lynch
Denis
D
Schaeffer
Marcel
M
Kissane
Marie
M
Chopra
Jay
J
O'brien
Elisabeth
E
Ford
Alan
A
Ferguson
George
G
Maguire
Anita R
AR
D000178:Acrylamides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013854:Thioamides / Q000737:chemistry*
D000178:Acrylamides; D013854:Thioamides