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 language | English |
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Pages (from-to) | 1228-1241 |
Number of pages | 14 |
Journal | Organic & Biomolecular Chemistry |
Volume | 5 |
DOIs | |
Publication status | Published - 2007 |
Keywords
- FRIEDEL-CRAFTS REACTION
- ORGANIC-SYNTHESIS
- LACTAMS
- CHLOROSULFIDES
- SOLVENTS
- AMIDES