Abstract
Replacement of a halogen substituent by hydrogen in the reaction of a perfluorophenyl halide which has a basic nitrogen substituent at the para -position with an aqueous hydrogen halide was investigated. The reaction behavior of p -halogeno-N,N-dimethylperfluoroanilines with various aqueous hydrogen halides and those of p -halogenoperfluorophenyltrimethylammonium trifluoromethanesulfonates with nucleophiles and electron-transferring agents indicated two plausible reaction mechanisms for the dehalogenohydrogenation in acid media: a reaction route via positive halogen transfer resulting from nucleophilic attack on the halogen substituent (S NX process) and that via electron-transfer and unimolecular elimination of halide ion (S RN1 process). The ammonio group and perfluoro substituents on the aromatic ring were found to be indispensable to allow this dehalogenohydrogenation.
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