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Relevant academic research and scientific papers

Synthesis and coordination chemistry of perfluoroalkyl-derivatised triarylphosphites

A series of ortho-, meta- and para-perfluoroalkyl-substituted triaryl phosphites have been prepared and their coordination chemistry investigated. Spectroscopic and structural data for the metal complexes indicate that, even with the additional oxygen spacer unit, complete electronic insulation of the phosphorus(III) centres is not achieved.

Partitioning solvophobic and dispersion forces in alkyl and perfluoroalkyl cohesion

Fluorocarbons often have distinct miscibility properties compared to their nonfluorinated analogues. These differences may be attributed to van der Waals dispersion forces or solvophobic effects, but their contributions are notoriously difficult to separate in molecular recognition processes. Here, molecular torsion balances were used to compare cohesive alkyl and perfluoroalkyl interactions in a range of solvents. A simple linear regression enabled the energetic partitioning of solvophobic and van der Waals forces in the self-association of apolar chains. The contributions of dispersion interactions in apolar cohesion were found to be strongly attenuated in solution compared to the gas phase, but still play a major role in fluorous and organic solvents. In contrast, solvophobic effects were found to be dominant in driving the association of apolar chains in aqueous solution. The results are expected to assist the computational modelling of van der Waals forces in solution.

Highly fluorous bidentate phosphines

The reaction of tetrachlorodiphosphines [Cl2P(CH 2)nPCl2; n = 2-4] with fluorous aromatic precursors 4-bromo(perfluorohexyl)benzene and 4-(perfluorohexyl)phenol gave a series of fluorous-tagged diphosphines [(p-C6F13C 6H4)2P(CH2)nP(C 6H4C6F13-p)2; n = 2-4] and a new diphosphonite [(p-C6F13C6H 4O)2P(CH2)3P(OC6H 4C6F13-p)2]. The improved synthesis of 1,3-bis(dichlorophosphino)propane (dcpp), involved the facile chlorination of the corresponding primary phosphine with triphosgene. Fluorinated diimines RN=C(CH3)C(CH3)=NR, where R = p-C6H 4C6F13 or P-C6H4C 8F17 have also been prepared, and were found to be air-stable alternatives to the highly air-sensitive phosphorus-containing ligands. All compounds were characterised by a variety of techniques including NMR, IR, MS and microanalysis. The successful reduction of the phosphine-oxides [(p-C6F13C6H4)2P(O) (CH2)nP(O)(C6H4C6F 13-p)2; n = 2,3] with phenylsilane is also presented. Georg Thieme Verlag Stuttgart.

Perfluoroalkylations and perfluorooxaalkylations. Part 4. Conversion of aryl perfluoroalkanes to aryl perfluoroalkyl ketones

The hydrolysis of benzylic fluorines with hydrobromic acid in glacial acetic acid has been utilized to convert some substituted phenyl perfluoroalkanes to the corresponding ketones.Electron-donating substituents such as -OMe, -OH or -NH2 on the benzene ri

Phosphorus(III) ligands in fluorous biphase catalysis

The synthesis, coordination chemistry and catalytic applications of a series of perfluoroalkyl-substituted phosphorus(III) ligands is illustrated.

Phosphorus(III) ligands with fluorous ponytails

A series of phosphorus(III) compounds incorporating one or more C6F13 'ponytails' have been prepared as a pool of ligands for coordination and catalytic studies under the fluorous biphase regime. Solubility studies indicate that only ligands with three or more ponytails are preferentially soluble in perfluorocarbon solvents.