- Direct Observation of Simple Fluorinated Carbanions
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Simple perfluorinated carbanions are generated and observed by (19)F and (13)C n.m.r. spectroscopy; curious low-field shifts are observed for sites adjacent to the charged centres.
- Bayliff, Andrew E.,Bryce, Martin R.,Chambers, Richard D.,Matthews, Raymond S.
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- REACTIONS OF TERTIARY PERFLUOROALKYL HALIDES WITH HALIDE ANIONS
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The reactivities of the F-tert.-alkyl halides (CF3CF2CF2(CF3)2CX (1a-c: X = I, Br Cl)) towards the corresponding lithium halides LiY (2a-c: Y = I, Br, Cl), in acetonitrile, reflect the electron acceptor properties of compounds 1 and the donator strength of the anions Y(1-).The tertiary carbanion F-2-methylpentanide acts as the key intermediate in the formation of the main products (F-2-methyl-2-pentene, F-2-methyl-1-pentene and F-2-hydro-2-methylpentane), and also of the halide substitution products obtained from 1a.No support for the participation of any perfluoroalkyl radical could be found.
- Blume, Elisabeth,Gasafi-Martin, Waltraud,Probst, Anton,Werner, Konrad von
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p. 387 - 396
(2007/10/02)
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- REACTIONS INVOLVING FLUORIDE ION. PART 34. STABLE PERFLUORINATED CARBANIONS
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A remarkable series of perfluoroalkyl anions, generated by reaction of caesium fluoride with various perfluorinated alkenes have been observed by (19)F and (13)C n.m.r. spectroscopy.Trapping experiments are described and threshold temperatures are established for the onset of fluoride ion exchange.The effects of counter ions are compared and (Me2N)3S+ (TAS) salts are more readily produced than Cs+ salts, but exchange of fluoride ion with fluorinated alkenes occurs more readily with TAS salts.Ph4P+ and Bu4N+ salts could not be obtained.Competition experiments for CsF between various perfluoroalkenes has established orders of carbanion stability.
- Bayliff, Andrew E.,Chambers, Richard D.
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p. 201 - 208
(2007/10/02)
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- Stable Perfluoroalkyl Carbanion Salts
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The synthesis and properties of tris(dimethylamino)sulfonium (TAS) salts of perfluoro tertiary carbanions are desribed.Many of these unique salts are isolable and stable up to their melting points, and they dissolve in organic solvents to provide high concentrations of perfluoro carbanions.Several reactions of TAS+CF3CF2CF2C-(CF3)2, which exemplify the synthetic utility of these new salts, are reported.
- Smart, Bruce E.,Middleton, William J.,Farnham, William B.
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p. 4905 - 4907
(2007/10/02)
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- Tris(disubstituted amino)sulfonium perfluorocarbanion salts
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Tris(disubstituted amino)sulfonium perfluorocarbanion salts and process for their preparation.
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