title: Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of alpha-thioamides to alpha-thio-beta-chloroacrylamides.
abstract: 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.
authors.affiliation: Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland.
authors.forename: Maureen
authors.initials: M
authors.lastname: Murphy
authors.forename: Denis
authors.initials: D
authors.lastname: Lynch
authors.forename: Marcel
authors.initials: M
authors.lastname: Schaeffer
authors.forename: Marie
authors.initials: M
authors.lastname: Kissane
authors.forename: Jay
authors.initials: J
authors.lastname: Chopra
authors.forename: Elisabeth
authors.initials: E
authors.lastname: O'brien
authors.forename: Alan
authors.initials: A
authors.lastname: Ford
authors.forename: George
authors.initials: G
authors.lastname: Ferguson
authors.forename: Anita R
authors.initials: AR
authors.lastname: Maguire
mesh_terms: D000178:Acrylamides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013854:Thioamides / Q000737:chemistry*
chemical_list: D000178:Acrylamides; D013854:Thioamides