Aromatic compounds with new fluorine-containing substituents |
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| Institution: | 1. College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, PR China;2. National Engineering Research Center for Dyeing and Finishing of Textiles, Donghua University, Shanghai, 201620, PR China;1. Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 95, CZ-532 10, Pardubice, Czech Republic;2. SYNPO, a.s., S. K. Neumanna 1316, CZ-532 07, Pardubice, Czech Republic;3. Eenheid Algemene Chemie (ALGC), Member of the QCMM VUB-UGent Alliance Research Group, Vrije Universiteit Brussel, Pleinlaan 2, 1050, Brussels, Belgium |
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| Abstract: | The introduction of strong electron-accepting fluorine-containing substituents into the aromatic moiety gives compounds with unique properties. Determination of the electronic nature of the grouping (Rf)2PO in arylbis(perfluoroalkyl)-phosphine oxides has shown that this substituent is comparable with RfSO2, one of the most electron-accepting groups.A general principle is proposed for the construction of the new superstrong electron-accepting substituents by the replacement of oxygen atoms for trifluoromethylsulfonylimino groups. For example, when the oxygen atoms in CF3SO and CF3SO2 groups are replaced by CF3SO2N=, new stable and even more electron-accepting substituents are formed. The grouping CF3S(O)=NSO2CF3 corresponds to two nitro groups. A similar increase in electron-accepting ability is observed in groupings derived from other elements by replacement of oxygen atoms by the CF3SO2N= group. |
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