REACTION OF TRIFLUOROMETHYLSULFENYL CHLORIDE WITH 3-CHLORO- AND 3-HYDROXYPROPYNES

Abstract

Vinylsulfides are often obtained via the reaction of substituted acetylenes with sulfur-containing reagents. The presence of other functional groups such as the halide or the hydroxyl moieties enhances the usefulness of the vinylsulfide intermediates. To this end, propargyl alcohol and halides have found wide application. With a view to enhance the biological properties of the end products synthesized from the vinylsulfide intermediates, the trifluoromethylthio function has now been incorporated as a part of the vinylic system. This communication presents the free-radical addition of trifluoromethylsulfenyl chloride to 3-chloro- and 3-hydroxypropynes, and the mechanism of the formation of the various products and their spectral characterization.

Keywords:

• Multiple bonds
• novel free-radical reactions and addition products
• trifluoromethylsulfenyl chloride
• vinylsulfides

Presented at the 12th European Symposium on Fluorine Chemistry, Berlin (Germany), 29 Aug. to 2 Sep. 1998; Abst. PII-68.