- Complexation and Photoinduced Electron-transfer Reaction between Perfluoroalkyl Iodides and N,N,N',N'-Tetramethylphenylene-1,4-diamine, Anilines and Piperazines
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Treatment of tetrafluoro-1,2-diiodoethane 1a or dodecafluoro-1,6-diiodohexane 1b with N,N,N',N'-tetramethylphenylene-1,4-diamine 2 gave 1 + 1 solid complexes 3a or 3b in high yields.Complex 3a decomposed to give tetrafluoroethylene, iodine and 2 when irradiated with UV or heated.Complex 3b was converted into 6H-dodecafluorohexyl-N,N,N',N'-tetramethylphenylene-1,4-diamine 4 when irradiated with UV.On treatment of 1a and 1b with piperazine 6a and N,N'-dimethylpiperazine 6b, 1 + 1 solid complexes 7 were similarly obtained.However, heating or irradiating 7 gave no perfluoroalkylated products.Irradiating a mixture of 2 or anilines 13 and perfluoroalkyl iodides 10 in dimethylformamide also gave perfluoroalkylated products.The photoinduced electron transfer reaction involved radical cation 2*+ as a reactive intermediate which was detected by EPR techniques.
- Chen, Qing-Yun,Li, Zhan-Ting,Zhou, Cheng-Min
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p. 2457 - 2462
(2007/10/02)
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- DIRECT PERFLUOROALKYLATION OF FUNCTIONALIZED BENZENES WITH PERFLUOROALKYL HALIDES AND COPPER BRONZE
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Perfluoroalkyl halides were found to react with functionalized benzenes in the presence of copper bronze to give the corresponding perfluoroalkylated products directly in moderate to good yields.The reaction may involve' active species' other than perfluoroalkylcopper species.Synthetic utility and possible mechanisms of the present one-step reaction are discussed.
- Fuchikami, Takamasa,Ojima, Iwao
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p. 541 - 556
(2007/10/02)
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- PERFLUOROALKYLATION OF AROMATIC COMPOUNDS WITH RfI(Ph)OSO2CF3
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Perfluoroalkylation of various aromatic compounds with perfluoroalkylphenyliodonium trifluoromethanesulfonate (FITS) under mild conditions was described.The reactivity of other perfluoroalkyliodonium salts was also examined.
- Umemoto, Teruo,Kuriu, Yuriko,Shuyama, Hideo
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p. 1663 - 1666
(2007/10/02)
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