Fluoroalkene chemistry: Part 3. Reactions of arylthiols with perfluoroisobutene, perfluoropropene and chlorotrifluoroethene |
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Authors: | Christopher M Timperley Matthew J Waters Jackie A Greenall |
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Institution: | Defence Science and Technology Laboratory, Porton Down, Salisbury, Wiltshire SP4 0JQ, UK |
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Abstract: | 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)2C C(SAr)2 and with 2-methoxybenzenethiol to give mono- and bis-vinyl species (CF3)2C CFSAr and (CF3)2C C(SAr)2. PFP reacted with both thiols to give the addition product CF3CFHCF2SAr and vinyl isomers CF3CF CFSAr (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. |
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Keywords: | Chlorotrifluoroethene Perfluoroisobutene Perfluoropropene Thiol Toxicity |
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