Fluoroalkene chemistry: Part 3. Reactions of arylthiols with perfluoroisobutene, perfluoropropene and chlorotrifluoroethene

Reactions of perfluoroisobutene (PFIB), perfluoropropene (PFP) and chlorotrifluoroethene (CTFE) with benzenethiol and 2-methoxybenzenethiol in acetonitrile, with potassium carbonate as base, were compared. PFIB reacted with benzenethiol to give ketene thioacetal (CF3)2CC(SAr)2 and with 2-methoxybenzenethiol to give mono- and bis-vinyl species (CF3)2CCFSAr and (CF3)2CC(SAr)2. PFP reacted with both thiols to give the addition product CF3CFHCF2SAr and vinyl isomers CF3CFCFSAr (6:1 E/Z ratio). CTFE reacted with several methoxy-substituted arylthiols to give addition products of structure CFClHCF2SAr. The arylthiols used throughout the study imitate biological thiols. Inhalation toxicities of the fluoroalkenes decrease in the order PFIB > PFP > CTFE and correlate with their reactivities towards the model thiols, supporting the current view that their toxicity relates to their ability to react with biological thiols.

Products from reaction of the above fluoroalkenes with benzenethiol and 2-methoxybenzenethiol are described. Figure optionsDownload as PowerPoint slide