Diphenylphosphinic fluoride

Diphenyltrifluorophosphorane is a colorless liquid, markedly more stable in the atmosphere and toward glass than phenyltetrafluorophosphorane or dialkyltrifluorophospho-ranes. Hydrolysis leads to diphenylphosphinic fluoride and, ultimately, to diphenylphosphinic acid. The fluoro-phosphorane can be stored in glass bottles over prolonged periods. The reported boiling point is 106 to 107°/2 mm., and the refractive index n = 1.5410. (The checkers report 1.5413 at 20°.)... 

Bis[l,2-bis(diphenylphosphine)ethane]-palladium(O), 34 Tributyl(iodomethyl)tin, 314 Other alkylations Dichlorodimethyltitanium, 216 Potassium fluoride, 256 (S)-Prolinol, 261... 

Diphenyltrifluorophosphorane was first obtained by the reaction of diphenylphosphinic acid with sulfur (IV) fluoride under autogenous pressure. The present method consists in the reaction of diphenylchlorophosphine with arsenic(III) fluoride at atmospheric pressure. ... 

On the synthetic side, single diastereomers of P-keto phosphine oxides have been generated from intermolecular acylation of phosphine oxides using either chiral esters or chiral phosphine oxides. In most cases, reduction of the ketone products was not affected by the presence of extra chiral centres. Addition of metallated phosphine oxides to proline-derived ketoaminals provides a new route to optically active P-hydroxy phosphine oxides. The P-hydroxy phosphine oxide 97 has been prepared by the caesium fluoride mediated reaction of silyl-substituted phosphine oxide 98 and benzaldehyde." The synthesis of two (E)-(6-hydroxy-2-hexen-l-yl)diphenylphosphine oxides (99) has been reported. The Horner-Wittig reactions of these compounds with various carbonyl compounds... 

The hexafluorophosphate ion has proved to be very useful for studies with complexes, since the [PF6] anion has a very weak coordinating ability.1 Lan-thanoid hexafluorophosphates can be obtained in very concentrated aqueous solutions by reaction of a freshly prepared solutions of hexafluorophosphoric acid and a hydrated lanthanoid basic carbonate.2 The resulting solution, after filtration, is evaporated to near dryness. Attempts to isolate the hydrated salts are unsuccessful because of decomposition accompanied by hydrogen fluoride evolution. Nevertheless, the complexes containing diphenylphosphinic amide are isolable and are quite stable.3... 

Studies on the alkaline hydrolysis of various phosphonic and phosphinic esters have provided information on the electronic or steric effects of substituents and the effects of changes in reaction conditions amongst the substrates so extensively examined are the O-aryl esters of dimethylphosphinothioic acid (552) esters of diphenylphosphinic acid and O-aryfand S -aryf esters of diphenylphosphinothioic acid (553 Z, Y = O or S). Other studies have concentrated on aryl esters of diaryIphosphinic acids (554) , and the effects of the stepwise replacement of P-Me by P-Ph in esters of dimethyl-, methylphenyl- and diphenyl-phosphinic acids The esters 555 (R = EtO, R = Me or Ph, R = R = Ph X = SEt or hydrolyse under alkaline conditions faster than do the comparable 5 -(4-substituted-butyl) esters. Comparable steric and electronic influences on the hydrolyses of phosphonic and phosphinic fluorides phosphinic chlo-rides the phosphonothioic chlorides 556 and other phosphonic and phosphinic esters have been noted. Phosphonic and phosphinic halides are prone to undergo halo-gen-exchange reactions, a process which, in general, is faster for derivatives of phosphonic than for those of phosphonothioic and phosphonoselenoic acids, and to be particularly important for acid fluorides . ... 

Lithium dimethyl cuprate, 209-215 Lithium diphenylarsenide, 341 Lithium diphenyl cuprate, 234 Lithium diphenylphosphide, 340-341, 645 Lithium diphenylphosphinate, 340 Lithium di-n-propyl cuprate, 245 Lithium ethynyltrialkylborates, 324-325 Lithium fluoride, 17... 

Oshima and coworkers have reported that treatment of tertiary alkyl fluorides with diphenylphosphine in the presence of a stoichiometric amount of BF3 OEt2 gives rise to the corresponding tert-alkyldiphenylphosphine tetrafluoroborate salts, which can be trapped by elemental sulfur to give the phosphine sulfides (144) (Equation 86) [88]. Remarkably, this reaction works despite the presence of the highly coordinating Lewis basic phosphine. 

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