137730-96-2Relevant academic research and scientific papers
Fluoro-organic sulphur-containing compounds. IV. Haloalkylation reactions of polyfluorinated thiophenols with CHal3R compounds in the presence of AlCl3: Synthesis and some reactions of polyfluorophenylthio derivatives of halomethanes
Petrova,Platonov,Maksimov
, p. 17 - 28 (2007/10/03)
The haloalkylation of polyfluorothiophenols with CHal3R compounds (Hal=Cl, F; R=Cl, H, C6H5, C6F5) in the presence of AlCl3 has been investigated. The reactions of polyfluorothiophenols 4-XC6F4SH (X=F, H, CH3) with CCl4 and AlCl3 lead to dichloromethane derivatives (4-XC6F4S)2CCl2. The reaction of pentafluorothiophenol with CHCl3 in the presence of AlCl3 gave (C6F5S)2CHCl and (C6F5S)3CH (ratio by GLC 8:1). In the reaction of pentafluorothiophenol with ArCX3 (Ar=C6H5, C6F5; X=Cl, F) compounds (C6F5S)2CClAr (Ar=C6H5, C6F5) together with C6F5SCCl2Ar (Ar=C6H5, C6F5) are formed. Peculiarities of these processes are considered. The hydrolysis of (C6F5S)2CCl2 and C6F5SCCl2C6H5 leads to bis(pentafluorophenyl)dithiocarbonate and the S-(pentafluorophenyl) ester of thiobenzoic acid, respectively. Compounds (C6F5S)2CF2 and (C6F5S)2CClF were obtained from (C6F5S)2CCl2 by the action of caesium fluoride. An attempt to produce these compounds through the action of antimony fluorides was unsuccessful. The compounds (C6F5S)2CCl2, (C6F5S)2CClF and (C6F5S)2CF2 are stable to oxidation. The reactions of (C6F5S)2CF2 and (C6F5S)2CClF with CrO3 in acetic acid proceeded only with the formation of mono-sulphoxide. The conversion is low in the former case.
