38550-45-7Relevant articles and documents
Synthesis and characterization of a new class of polyfluorinated alkanes: Tetrakis(perfluoroalkyl)alkane
Gambaretto,Conte,Fornasieri,Zarantonello,Tonei,Sassi,Bertani, Roberta
, p. 57 - 63 (2003)
The synthesis and physico-chemical characterization of 1,1,2,2-tetrakis(perfluoroalkyl-methylene)ethane {[F(CF2)nCH2]2CH}2 (n=6, TK6;n=8, TK8 ) are reported. The synthesis consists of four steps: (1) addition of allyl alcohol to a perfluoroalkyl iodide, F(CF2)nI(n=6,8) to give the corresponding iodo-adduct; (2) dehalogenation of the adduct by treatment with zinc in aqueous acetic acid, yielding 3-perfluoro-n-alkyl-1-propene; (3) addition of 3-perfluoro-n-alkyl-l-propene to perfluoroalkyl iodide, F(CF2)nI (n=6,8) to give 1,3-perfluoro-n-alkyl-2-iodo-propane; (4) coupling of 1,3-perfluoro-n-alkyl-2-iodo-propane by zinc in acetic anhydride giving the final products. TK6 and TK8 are characterized by very low surface tension values and exhibit very good properties as potential ski-waxes.
Regioselective ring opening of [(perfluoroalkyl)methyl] oxiranes with N-nucleophiles
Conte,Maniero,Zaggia,Bertani,Gambaretto,Berton,Seraglia
, p. 1274 - 1280 (2005)
The reactions of C8F17CH2CHCH2O with some primary and secondary aliphatic amines affording selective ring opening at Cβ are reported. The reactions with secondary amines HNR1R2 (R1 = R2 = Et; R1 = But, R2 = CH2CH2O(CO)C(CH 3)CH2; R1 = Et, R2 = CH 2CH2OH; R1 = R2 = CH 2CH2OH) gave the corresponding C8F 17CH2CH(OH)CH2NR1R2 derivatives. For R1 = Et, R2 = CH2CH 2OH; R1 = R2 = CH2CH2OH, the reactions proceed through the selective nucleophilic attack of the NH moiety with no evidence of reactivity of the OH group. The reactions with the primary amines, allylamine and n-hexamethylenediamine, gave different products depending on reaction conditions.
Benzophenone vs. Copper/Benzophenone in Light-Promoted Atom Transfer Radical Additions (ATRAs): Highly Effective Iodoperfluoroalkylation of Alkenes/Alkynes and Mechanistic Studies
Beniazza, Redouane,Atkinson, Rachel,Absalon, Christelle,Castet, Frédéric,Denisov, Sergey A.,McClenaghan, Nathan D.,Lastécouères, Dominique,Vincent, Jean-Marc
, p. 2949 - 2961 (2016/09/16)
Iodoperfluooralkylation of terminal alkenes and alkynes is effectively photo-promoted by benzophenone 2 (BP) or the photoreducible copper(II) complex 1. In particular, BP at 1 mol% in methanol upon 365 nm irradiation with a low-pressure mercury lamp (type TLC=thin layer chromatography, 6 W) results in a fast reaction with excellent reaction yields. Complex 1 and BP 2 exhibited very similar reactivity, suggesting that the reactions involving 1 are likely to be governed by the benzophenone photoactivation processes, rather than copper(I)/(II) redox processes. Mechanistic investigations using transient absorption spectroscopy revealed that a deactivation pathway of the benzophenone triplet (3BP*) is via its reaction with the methanol solvent. We propose that the generated radicals, in particular.CH2OH, play a key role in the initiation step forming Rf.by reacting with RfI, Rf.then entering a radical chain cycle.1H NMR studies provided evidence that a substantial amount (～7% NMR yield) of the hemiacetal CH3OCH2OH is formed, i.e., the possible by-product of the reaction between.CH2OH and RfI. Finally, DFT calculations indicate that a triplet-triplet energy transfer (TTET) process from3BP* to perfluorooctyl iodide (C8F17I) is unlikely or should be rather slow under the reaction conditions, consistent with the transient absorption studies. (Figure presented.).
Mesophase structure of low-wetting liquid crystalline polyacrylates with new perfluoroalkyl benzoate side groups
Martinelli, Elisa,Paoli, Francesca,Gallot, Bernard,Galli, Giancarlo
experimental part, p. 4128 - 4139 (2011/10/30)
The synthesis, thermal behavior, bulk microstructure, and wettability of new polyacrylates carrying spaced 4-perfluorohexylpropyl benzoate and 4-perfluorooctylpropyl benzoate units in the side groups were Investigated. X-ray diffraction analysis proved the formation of different smectic mesophases (SmI2, SmF2, and SmC2) and the evolution of their structures and lattice parameters with temperature. The mesophase polymorphic behavior depended on the length of the perfluorinated chain segment in the repeat unit. The electron density profiles along the smectic layer normal were drawn and provided a deeper insight into the packing of the side chains in a tilted, double layer structure. Thin polymer films were cast from solution, and their low wettability was established by measurements of contact angles with different probing liquids. We suggest that the hydrophobicity and lipophobicity of the films are enhanced by the mesophase surface structure which is mediated by the high-order, mesophase bulk structure.
