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Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula P H 3, classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting fish, due to the presence of substituted phosphine and diphosphane ( P 2 H 4 ).
Lithium phospahnide can be made from phosphine and butyl lithium or phenyl lithium. [3] Another way to produce -PH 2 complexes is by hydrolysis of a -P(SiMe 3) 2 compound with an alcohol, such as methanol. [3] Yet another way is to remove a hydrogen atom from the phosphine in a phosphine complex by using a strong base. [3]
Phosphinous acids are usually organophosphorus compounds with the formula R 2 POH. They are pyramidal in structure. Phosphorus is in the oxidation state III. Most phosphinous acids rapidly convert to the corresponding phosphine oxide, which are tetrahedral and are assigned oxidation state V.
Tertiary phosphines characteristically oxidize to give phosphine sulfides. The reducing properties of organophosphiines is also illustrated in the Staudinger reduction for the conversion of organic azides to amines and in the Mitsunobu reaction for converting alcohols into esters. In these processes, the phosphine is oxidized to phosphorus(V).
Compounds related to phosphine oxides include phosphine imides (R 3 PNR') and related chalcogenides (R 3 PE, where E = S, Se, Te). These compounds are some of the most thermally stable organophosphorus compounds. In general, they are less basic than the corresponding phosphine oxides, which can adduce to thiophosphoryl halides: [7]: 73
The first phosphorine to be isolated is 2,4,6-triphenylphosphorine. It was synthesized by Gottfried Märkl in 1966 by condensation of the corresponding pyrylium salt and phosphine or its equivalent ( P(CH 2 OH) 3 and P(SiMe 3) 3). [3] The (unsubstituted) parent phosphorine was reported by Arthur J. Ashe III in 1971.
Tris(o-tolyl)phosphine is an organophosphorus compound with the formula P(C 6 H 4 CH 3) 3. It is a white, water-insoluble solid that is soluble in organic solvents. In solution it slowly converts to the phosphine oxide. As a phosphine ligand, it has a wide cone angle of 194°.
Diphosphane, or diphosphine, is an inorganic compound with the chemical formula P 2 H 4. This colourless liquid is one of several binary phosphorus hydrides. It is the impurity that typically causes samples of phosphine to ignite in air.