- Reactions of aromatic compounds with xenon difluoride
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Reactions of substituted benzenes C6H5R (R = Me, F, Cl, Br, CF3, NO2) with xenon difluoride in the presence of boron trifluoride–diethyl ether complex in weakly acidic (1,1,1,3,3-pentafluorobutane) and weakly basic media (acetonitrile) have been studied. These reactions lead to the formation of fluorobenzene derivatives FC6H4R (isomer mixture) together with isomeric difluorobenzenes and fluorinated and non-fluorinated biphenyls. The results have been compared with previously reported data obtained in other solvents using other catalysts.
- Bardin,Adonin, N. Yu.
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p. 1400 - 1407
(2016/11/29)
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- Competitive fluorination on methyl-group and benzene-ring during the anodic fluorination of fluorotoluenes in Et4NF · mHF
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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.
- Momota, Kunitaka,Yonezawa, Tetsuo,Mukai, Katsuji,Morita, Masayuki
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p. 173 - 178
(2007/10/03)
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