- Convenient syntheses and characterization of fluorophilic perfluorooctyl-propyl amines and ab initio calculations of proton affinities of related model compounds
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A convenient and effective method for the preparation of perfluorooctyl-propyl amines ([Rf8(CH2)3]nNH3-n (1-3), n=1,2,3; Rf8(CH2)3NHMe (4); [Rf8(CH2)3]2NMe (5); Rf8(CH2)3NMe2 (6); Rf8=F(CF2)8) via a step by step alkylation with Rf8(CH2)3I is described. The fluorophilicity values of 1-6 were determined by GC and range from 0.79±0.07 (1) to 5.3±0.2 (3). Systematic ab initio calculations of proton affinities of model compounds (7a-j) using Hartree-Fock and density functional theory imply that the inserted trimethylene spacer unit efficiently reduces the electron-withdrawing effect of the perfluorinated segment. All structures were verified by multinuclear one- and two-dimensional NMR experiments involving both homo- (19F-19F) and hetero-nuclear (1H-13C, 1H-15N, 19F-13C) correlations based on the GMQFCOPS and inverse 1H and/or 19F detected GHSQC, GHMQC sequences with broadband adiabatic 13C-decoupling.
- Szlávik, Zoltán,Tárkányi, Gábor,G?m?ry, ágnes,Tarczay, Gy?rgy,Rábai, József
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- Improved synthesis of perfluorooctylpropyl amine
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Hydrazinolysis of N-perfluorooctylpropyl phthalimide is an easy route to scale up for the title compound. Both the alkylation of potassium phthalimide with perfluorooctylpropyl iodide and the hydrogenolysis of the adduct of perfluoroctyl iodide to N-allyl-phthalimide provide this amine precursor in good yields. The latter procedure, however, has a better atom economy, since it requires only three steps from perfluorooctyl iodide.
- Abulikemu, Abudurexiti,Halász, Gábor,Csámpai, Antal,G?m?ry, ágnes,Rábai, József
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p. 1143 - 1146
(2007/10/03)
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- Convenient syntheses of a family of easily recoverable fluorous primary, secondary and tertiary aliphatic amines NH(3-x[(CH2)(m)(CF2)7CF3](x) (m = 3-5; x = 1-3) - Fine tuning of basicities and fluorous phase aff
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The alcohols HOCH2(CH2)(m-1)(CF2)7CF3 [m = 3-5; (CF2)7CF3 = R(f8)] are oxidized to aldehydes O=CH(CH2)(m-1)R(f8) (Dess-Martin reagent, 90-96%), which are co
- Rocaboy, Christian,Bauer, Walter,Gladysz, John A.
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p. 2621 - 2628
(2007/10/03)
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- Lubricants and new polyfluorinated compounds which can be used as additives
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In order to improve the wear resistance properties of lubricants, at least one compound of the following formula is incorporated therein: STR1 Rf is a perfluorinated radical, a=0 to 10, b=0 or 1 (if a=o and c=1), c=1 to 4 (2 if a≠0), m=0 or 1, n=0 or 1, X
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