Triphenylphosphine sulphide

Pyridines, quinolines, triphenylphosphine, sulphides, selenides and thioureas are among such nucleophiles, which under the proper conditions, usually copper or light... 

Miscellaneous. The unusual reductions of benzyltriphenylphosphonium salts with sodium to give benzyldiphenylphosphine have been shown to involve reduction of the benzylidenephosphorane. This ylide with sulphur in benzene at 70 °C gave triphenylphosphine sulphide, a pentasulphide formulated as (45) or (46), and only traces of isomeric stilbenes. Previous workers reported high yields of stilbenes from the same reaction carried out in refluxing toluene. Benzoylmethylenetriphenylphosphorane (47) with sulphur gave a polymer of the thioaldehyde (48). 

The chemical and electrochemical oxidations of triphenylphosphine sulphide and phosphorothioates in acetonitrile have been investigated.In both reactions, triphenylphosphine sulphide initially gives a product formulated as a dimeric di-cation (39), but this rapidly decomposes on removal of the solvent or exposure to air. Triphenylphosphine oxide and sulphide form radical anions on treatment with potassium in ether at low temperature or by one-electron reduction at a Hg cathode in DMF. The photo-oxidation (sensitized by polymer-supported Rose Bengal) of triphenylphosphine selenide to the oxide has been shown to be highly solvent-dependent. 

Polarography has been used to anal) e the role of amine catalysts in phos-phonate hydrolyses. Voltammetry data is reported for triphenylphosphine sulphide triethyl phosphorothioate and various triphenylphosphonium salts and ylides. ... 

Activity in phosphine and phosphonium salt chemistry remains at a high level, although exceptional contributions have been rare. A convenient synthesis of 5-phenyldibenzophosphole by treatment of triphenylphosphine oxide with phenyllithium and the facile route to triphenylphosphine sulphides offered by the reaction of the corresponding phosphines with... 

Triphenylphosphine sulphide, (CgH5)3PS.i—Triphenylphosphine in carbon disulphide solution combines directly with sulphur to yield the sulphide, and thiocyanic acid or thiocyanogen also gives some sulphide when it reacts with the phosphine. The sulphide crystallises from alcohol in long, brilliant needles, M.pt. 150° to 151° C., readily soluble in alcohol, benzene, chloroform or carbon disulphide, insoluble in water or ether. 

Triphenylphosphine sulphide and diphenylketene in molecular proportions react to form triphenylphosphine oxide and thioketene. ... 

Triphenylphosphine-p-tolylimine, ( 6115)3 =N.C6H4.CH3, is isolated from triphenylphosphine and p-tolyl azide in 93 per cent, yield. It forms faintly yellow crystals from ether, M.pt. 134° to 135° . If carbon dioxide be passed into the molten compound, triphenylphosphine oxide and p-tolyh>ccyanate result, and with carbon disulphide, triphenylphosphine sulphide and p-tolylthiocarbimide are obtained. 

Other Reactions of Inorganic Ligands Triphenylphosphine removes one sulphur atom from the thiocumato-complex (12), giving triphenylphosphine sulphide, SPPhg. The reaction is second-order, with an activation energy of 7.8 1.0 kcal mol-. ... 

Intermediates in Reactions.— Attempts to prepare thiaziridines or selenaziridines by treatment of oxaziridines (133) with thiourea, potassium thiocyanate, potassium ethylxanthate, potassium selenoxanthate, and triphenylphosphine sulphide gave imines (135) instead, although... 

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