- A Diheteroatom Fluoroalkylation Reagent for Preparation of S- and N-Containing Fluoroalkyl Compounds and Sulfonic Acid Polymer
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The first stable diheteroatom fluoroalkylation reagent, 2-((2-azido-1-chloro-1,2,2-trifluoroethyl)thio)pyrimidine (ACTP), has been prepared by a novel method. By using this reagent, various fluorinated thioethers and sulfones have been successfully prepared. The dearylation and dearylation-oxidation of fluoroalkyl 2-pyrimidyl sulfone in one-pot reaction were investigated systematically, and the results demonstrated that both fluoroalkyl sulfinates and sulfonates could be obtained in high yields. In addition, ACTP proved to be useful for the preparation of a fluorinated sulfonic acid proton-exchange membrane.
- Dai, Jingwen,Li, Zili,Wang, Taisheng,Bai, Wei,Bai, Ruke
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- Chemistry of Halogenoperfluoroalkanes> Synthesis of Fluorinated Ethers and Thioethers via Radical or Anionic Intermediates
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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.
- Wakselman, Claude,Tordeux, Marc
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p. 4047 - 4051
(2007/10/02)
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