title: Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles.
abstract: Synthetically versatile conjugate addition of a range of carbon, nitrogen, oxygen, sulfur and selenium nucleophiles to the highly functionalised 2-thio-3-chloroacrylamides is described. The stereochemical and synthetic features of this transformation are discussed in detail. In most instances, the nucleophile replaces the chloro substituent with retention of stereochemistry. With the oxygen nucleophiles, a second addition can occur leading to acetals, while with the nitrogen nucleophiles, E-Z isomerism occurs in the resulting enamine derivatives. The ratio of the E/Z isomers can be rationalised on the basis of the substituent and the level of oxidation.
authors.affiliation: Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland.
authors.forename: Marie
authors.initials: M
authors.lastname: Kissane
authors.forename: Maureen
authors.initials: M
authors.lastname: Murphy
authors.forename: Elisabeth
authors.initials: E
authors.lastname: O'Brien
authors.forename: Jay
authors.initials: J
authors.lastname: Chopra
authors.forename: Linda
authors.initials: L
authors.lastname: Murphy
authors.forename: Stuart G
authors.initials: SG
authors.lastname: Collins
authors.forename: Simon E
authors.initials: SE
authors.lastname: Lawrence
authors.forename: Anita R
authors.initials: AR
authors.lastname: Maguire
mesh_terms: D000178:Acrylamides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D018011:Chalcogens / Q000737:chemistry*; D017606:Chlorine Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000178:Acrylamides; D018011:Chalcogens; D017606:Chlorine Compounds; D013438:Sulfhydryl Compounds; D002244:Carbon; D009584:Nitrogen