Fluorination with xenon difluoride. Reactions of phenyl-substituted olefins in the presence of trifluoroacetic acid |
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| Authors: | Marko Zupan Alfred Pollak |
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| Affiliation: | Department of Chemistry and “Jo?ef Stefan” Institute, University of Ljubljana, 61000 LjubljanaYugoslavia |
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| Abstract: | Trifluoroacetic acid-catalyzed liquid-phase fluorination with xenon difluoride of phenyl-substituted olefins, e.g. cis- and trans-1-phenylpropene and cis- and trans-stilbene, results in the formation of vicinal difluorides and fluoro-trifluoroacetates. The reaction is non-stereospecific. d,1-Erythro and d,1-threo fluoro-trifluoroacetates are formed in a highly regiospecific Markovnikov manner in 50% yield. The formation of β-fluorocarbonium ions is suggested. |
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