80791-09-9Relevant articles and documents
Heterogeneous photoinduced homolytic aromatic substitution of electron-rich arenes with perfluoroalkyl groups in water and aqueous media - A radical-ion reaction
Barata-Vallejo, Sebastian,Flesia, Marina Martin,Lantano, Beatriz,Argueello, Juan E.,Penenory, Alicia B.,Postigo, Al
, p. 998 - 1008 (2013/03/14)
The photoinduced electron transfer (PET) substitution reaction of electron-rich aromatic nuclei with perfluoroalkyl Rf groups was carried out in water or aqueous mixtures to render substitution products resulting from replacement of aromatic H atoms with the Rf moiety in good yields (57-88 %). Some mechanistic aspects are discussed, supporting the notion of a PET reaction leading to a classical radical homolytic aromatic substitution (HAS) followed by an electron transfer (ET) and then a proton transfer (PT) sequence. A radical mechanism superimposed on a redox process is proposed to account for product formation. Evidence for the radical cation species (as an initiation event) generated from electron-rich arenes in the presence of perfluoroalkyl halides is provided by the UV/Vis transient spectra obtained by Nanosecond Laser Flash Photolysis techniques. Copyright
Complexation and Photoinduced Electron-transfer Reaction between Perfluoroalkyl Iodides and N,N,N',N'-Tetramethylphenylene-1,4-diamine, Anilines and Piperazines
Chen, Qing-Yun,Li, Zhan-Ting,Zhou, Cheng-Min
, p. 2457 - 2462 (2007/10/02)
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.
PERFLUOROALKYLATION OF AROMATIC COMPOUNDS WITH RfI(Ph)OSO2CF3
Umemoto, Teruo,Kuriu, Yuriko,Shuyama, Hideo
, p. 1663 - 1666 (2007/10/02)
Perfluoroalkylation of various aromatic compounds with perfluoroalkylphenyliodonium trifluoromethanesulfonate (FITS) under mild conditions was described.The reactivity of other perfluoroalkyliodonium salts was also examined.
