123271-08-9Relevant academic research and scientific papers
Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles
Kissane, Marie,Murphy, Maureen,O'Brien, Elisabeth,Chopra, Jay,Murphy, Linda,Collins, Stuart G.,Lawrence, Simon E.,Maguire, Anita R.
supporting information; experimental part, p. 2452 - 2472 (2011/05/11)
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.
Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β- chloroacrylamides
Murphy, Maureen,Lynch, Denis,Schaeffer, Marcel,Kissane, Marie,Chopra, Jay,O'Brien, Elisabeth,Ford, Alan,Ferguson, George,Maguire, Anita R.
, p. 1228 - 1241 (2008/02/03)
Treatment of a series of α-thioamides with N-chlorosuccinimide results in efficient transformation to the analogous α-thio-β- 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. The Royal Society of Chemistry.
SEN-ELIMINATION OF HCL IN THE SERIES OF PARA-SUBSTITUTED PHENYLAMIDES OF ERYTHRO-2-METHYL(PHENYL)THIO-3-CHLOROBUTYRIC ACIDS
Talaikite, Z. A.,Mishkinene, V. A.,Rasteikene, L. P.
, p. 254 - 258 (2007/10/02)
The elimination of HCl in the series of para-substituted phenylamides of erythro-2-methyl(phenyl)thio-3-chlorobutyric acids in nonpolar solvents during reaction with tertiary amines takes place syn-stereospecifically with the formation of the para-substituted phenylamides of Z-2-methyl(phenyl)thio-2-butenoic acids.The reactivity of these phenylamides is closely described by the Hammett equation with positive values for the reaction constant ρ.
