Jump to main content
Jump to site search

Issue 8, 2007
Previous Article Next Article

Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β-chloroacrylamides

Author affiliations

Abstract

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.

Graphical abstract: Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β-chloroacrylamides

Back to tab navigation

Supplementary files

Publication details

The article was received on 19 Dec 2006, accepted on 13 Feb 2007 and first published on 08 Mar 2007


Article type: Paper
DOI: 10.1039/B618540A
Org. Biomol. Chem., 2007,5, 1228-1241

  •   Request permissions

    Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β-chloroacrylamides

    M. Murphy, D. Lynch, M. Schaeffer, M. Kissane, J. Chopra, E. O'Brien, A. Ford, G. Ferguson and A. R. Maguire, Org. Biomol. Chem., 2007, 5, 1228
    DOI: 10.1039/B618540A

Search articles by author

Spotlight

Advertisements