Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of alpha-thioamides to alpha-thio-beta-chloroacrylamides

Maureen Murphy, Denis Lynch, Marcel Schaeffer, Marie Kissane, Jay Chopra, Elisabeth O'Brien, Alan Ford, George Ferguson, Anita R. Maguire

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1228-1241
Number of pages14
JournalOrganic & Biomolecular Chemistry
Volume5
DOIs
Publication statusPublished - 2007

Keywords

  • FRIEDEL-CRAFTS REACTION
  • ORGANIC-SYNTHESIS
  • LACTAMS
  • CHLOROSULFIDES
  • SOLVENTS
  • AMIDES

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