Journal of Fluorine Chemistry p. 173 - 178 (1998)
Update date:2022-08-04
Topics:
Momota, Kunitaka
Yonezawa, Tetsuo
Mukai, Katsuji
Morita, Masayuki
Electrochemical fluorinations of 2-fluorotoluene (2a), 3-fluorotoluene (3a) and 4-fluorotoluene (4a) in neat Et4NF · mHF (Et = C2H5, m = 3.5 or 4.0) were carried out on a platinum anode. The fluorination of 2a, 3a and 4a occurred competitively both on the side-chain (formation of monofluoromethylfluorobenzenes) and on the benzene-ring (formation of methyltrifluoro-1,4-cyclohexadienes). These results are explained by the facility of proton elimination from the methyl groups of the radical cations which have been formed by the anodic one-electron transfer reactions of 2a, 3a and 4a. A cyclic voltammogram of 4a showed three anodic current peaks which correspond to the oxidation of 4a, 1-fluoromethyl-4-fluorobenzene (4b) and 1-difluoromethyl-4-fluorolbenzene (4c). On the other hand, voltammograms of 2a and 3a showed two anodic current peaks and no difluoromethylfluorobenzenes was obtained during the fluorination of 2a and 3a.
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