85554-53-6Relevant academic research and scientific papers
Microwave-assisted aliphatic fluorine-chlorine exchange using triethylamine trihydrofluoride (TREAT-HF)
Kremsner, Jennifer M.,Rack, Michael,Pilger, Christian,Oliver Kappe
supporting information; experimental part, p. 3665 - 3668 (2009/10/04)
Aliphatic fluorine-chlorine exchange reactions can be performed under microwave conditions using TREAT-HF as a mild and selective fluorination reagent. The highly polar TREAT-HF couples efficiently with microwave irradiation and reaction temperatures of 250 °C can be reached within 30 s. Under these conditions dichloromethyl- and trichloromethyl substrates can be converted into the corresponding fluoro analogs within 5 min. In order to prevent corrosion of borosilicate reaction vessel at high temperatures the use of sintered silicon carbide microwave vials is introduced.
Chlorodifluoromethyl phenyl sulfone: A novel non-ozone-depleting substance-based difluorocarbene reagent for O- and N-difluoromethylations
Zheng, Ji,Li, Ya,Zhang, Laijun,Hu, Jinbo,Meuzelaar, Gerrit Joost,Federsel, Hans-Juergen
, p. 5149 - 5151 (2008/09/18)
Chlorodifluoromethyl phenyl sulfone, a previously unknown compound that can be readily prepared from non-ODS-based precursors, was found to act as a robust difluorocarbene reagent for O- and N-difluoromethylations. The Royal Society of Chemistry.
An efficient preparation of new sulfonyl fluorides and lithium sulfonates
Toulgoat, Fabien,Langlois, Bernard R.,Medebielle, Maurice,Sanchez, Jean-Yves
, p. 9046 - 9052 (2008/03/27)
(Formula Presented) An efficient preparation of several polyfluoroalkanesulfonyl fluorides is reported. This method, based on the synthesis of polyfluoroalkyl trimethyl silanes (precursors of polyfluoroalkylsulfinates) as intermediates, allows the successive transformations to be carried out in one pot. Moreover, these sulfonyl fluorides can be obtained from the corresponding sulfinates by electrophilic fluorination. This original approach avoids isolation and purification of some thermally or hydrolytically unstable intermediates. A series of new sulfonyl fluorides have been thus prepared from halogenodifluoromethylated precursors RCF2X (X = F, Br; R = ArC(O), ArS(O)n(CF2) m; n = 0, 1, 2; m = 1, 2) and have been transformed into the corresponding lithium sulfonates, which have potential applications as electrolytes for lithium batteries.
Reactions of Bromotrifluoromethane and Related Halides. Part 12. Transformation of Disulfides into Perfluoroalkyl Sulfides in the Presence of Sulfoxylate Anion Radical Precursors
Clavel, Jean-Louis,Langlois, Bernard,Nantermet, Roland,Tordeux, Marc,Wakselman, Claude
, p. 3371 - 3376 (2007/10/02)
Perfluoroalkyl sulfides are prepared by reaction of perfluoroalkyl halides with disulfides in the presence of sulfoxylate anion radical precursors.Aliphatic, aromatic and heteroaromatic disulfides bearing cyano, ester and amino functional groups have been employed; a variety of perhalogenoalkanes can also be employed, e.g.CF3(CF2)nI, CF3Br, CF2Br2, CF2BrCl, CFCl3 and CF2ClCFCl2.The most convenient sulfoxylate anion radical precursor for this reaction is formed by a combination of sodium formate and sulfur dioxide.
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.
SRN1 Substitutions of Halogenoperfluoroalkanes (CF3Br or CF2Cl2) under Pressure
Wakselman, Claude,Tordeux, Marc
, p. 793 - 794 (2007/10/02)
Radical chain fluoroalkylation of arenethiolates by CF3Br or CF2Cl2, performed under slight pressure in a glass apparatus, gives aryl polyfluoromethyl sulphides.
Reactivity of the Perhaloalkanes CF2X2 (X = Cl, Br) with Nucleophiles. 6. Coexistence of Carbene and Radical Processes Initiated by Single-Electron Transfer
Rixo, I.,Cantacuzene, D.,Wakselman, C.
, p. 1979 - 1982 (2007/10/02)
In the condensation of sodium thiophenoxide with CF2BrCl in DMF at -40 deg C, two mechanisms are involved simultaneously.A carbene chain process is postulated for the formation of C6H5SCF2Br and C6H5SCF2H.A radical chain process is implicated for the formation of C6H5SCF2Cl and C6H5SCF2SC6H5.These competitive chain processes could occur after an initial one-electron transfer from the thiophenoxide to CF2BrCl, giving a caged intimate radical/anion radical pair (RARP).
