Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of alpha-thioamides to alpha-thio-beta-chloroacrylamides |
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Authors: | Murphy Maureen Lynch Denis Schaeffer Marcel Kissane Marie Chopra Jay O'brien Elisabeth Ford Alan Ferguson George Maguire Anita R |
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Institution: | Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland. |
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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. |
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