A NEW SYNTHETIC APPROACH TO PERFLUOROCHEMICALS: LIQUID PHASE PHOTOFLUORINATION WITH ELEMENTAL FLUORINE. PART I

Article abstract of DOI:10.1016/S0022-1139(00)82178-8

This paper describes a novel, safe, effective technique, with a new reactor design, for the synthesis of perfluorochemicals.This method, the liquid-phase photofluorination with undiluted fluorine, is appicable to the preparative-scale synthesis of isomerically-pure branched F- alkanes, F-ethers and F-tert-amines which are difficult to prepare by the classical fluorination methods (i.e. electrochemical or CoF3).The technique is based on the controlled inverse addition of the materials to be fluorinated to a well-stirred F2-saturated inert solvent, with simultaneous UV irradiation.The application of this method to the synthesis of F-ethers is described: the following were made by this method, F-2-propoxy-2-methyl-pentane, F-2-isobutoxy-2-methylpentane, F-n-heptylpropylether, F-2-pentoxy-2-methoxypropane, F-3-propoxy-2-methylpentane, F-2-ethyl-2-isopropyltetrahydrofuran, F-3-isobutoxy-2-methylpentane, F-2-methoxy-4-ethyl-4-methylhexane, and F-2-methyl-(1-ethyl-1-methylpropyl)oxetane.