91122-73-5Relevant academic research and scientific papers
DISTINCTIVE AND SOLVENT-DEPENDENT BEHAVIOUR OF SOME PER(CHLORO,FLUORO)ETHANES IN THEIR REACTIONS WITH PhSNa. COMPETING MECHAMISTIC PATHWAYS IN HALOPHILIC REACTIONS
Li, Xing-ya,Pan, He-qi,Fu, Wei-min,Jiang, Xi-kui
, p. 213 - 230 (1986)
Per(chloro,fluoro)ethanes CF2XCCl2Y (1) react spontaneously with PhSNa at room temperature or below to give PhSCF2CCl2Y (2) in fair to good yield, which as well as the by-products PhSCF2CClYH (3) and PhSCF=CCl2 (4) (for 1b and 1c) are most probably produced by an anionic chain process initiated by the chlorophilic attack of PhS- on C-Cl bonds.In case of 1c, the coexistence of two competitive reaction pathways is indicated by the two products 2b and PhSCCl2CF3 (10).The reaction rates and the product distribution have been found to be highly solvent-dependent.Products 2b, 4 and 10 all react further with PhSNa to afford multi-substituted ethylenes PhSCF=C(Cl)SPh (7) (PhS)2C=C(Cl)SPh (8) and (PhS)2C=C(SPh)2 (9).
Chain-radical fluoroalkylation of thiophenols with freon ClCF2CFCl2 in the presence of sulfur dioxide
Koshechko, Vyacheslav G.,Kiprianova, Lydiya A.,Kalinina, Ludmyla I.
experimental part, p. 317 - 320 (2009/12/01)
A polyfluoroalkylation of thiophenols with CF2ClCFCl2 using substituted pyridine-sulfur dioxide system enables to obtain fluoroalkylated thioethers by a SRN1-type free-radical route.
SYNTHESIS OF FLUORINATED VINYL SULFIDES AND SELENIDES
Piettre, S.,de Cock, Ch.,Merenyi, R.,Viehe, H.G.
, p. 4309 - 4320 (2007/10/02)
The reaction between fluoroolefins 1 and 10e and benzenesulfenyl or selenenyl halides 6 is found to be solvent-dependent and gives in most cases predominantly the regioisomer 8.The structure of adducts 8 and 9 are ascertained by 1H, 19F and 77Se NMR spectroscopy.Compounds 8 are easily halogenated and treatment of the products with magnesium or zinc leads to the desired polyfluorovinyl sulfides and selenides 10.A second route of synthesis of these reagents results from the reaction of fluorovinyllithio-derivatives 11 with benzenesulfenyl or selenenyl halides.Olefin 10e is also obtained from the selenoacetal 8t of trifluoroacetaldehyde.
Chemistry of Halogenoperfluoroalkanes> Synthesis of Fluorinated Ethers and Thioethers via Radical or Anionic Intermediates
Wakselman, Claude,Tordeux, Marc
, p. 4047 - 4051 (2007/10/02)
Condensation of bromotrifluoromethane with potassium thiophenoxides in DMF is performed under pressure (2-3 atm) in a glass apparatus.Inhibition by nitrobenzene shows that a SRN1 mechanism is involved in the formation of aryl trifluoromethyl sulfides.Dichlorodifluoromethane itself reacts through a similar process to give aryl chlorodifluoromethyl sulfides.Condensation of 1,1,2-trichlorotrifluoroethane with potassium thiophenoxide or phenoxide occurs even in the presence of nitrobenzene.The formation of aryl 2,2-dichloro-1,1,2-trifluoroethyl sulfides or ethers can be explained by a chain carbanionic mechanism.
