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Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C 6 H 5) 3 and often abbreviated to P Ph 3 or Ph 3 P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic ...
Although ylides are "electron-rich", they are susceptible to deprotonation of alkyl substituents. Treatment of Me 3 PCH 2 with butyl lithium affords Me 2 P(CH 2) 2 Li. [3] Having carbanion-like properties, lithiated ylides function as ligands. Thus Me 2 P(CH 2) 2 Li is a potential bidentate ligand. [4]
Triphenylphosphine oxide (often abbreviated TPPO) is the organophosphorus compound with the formula OP(C 6 H 5) 3, also written as Ph 3 PO or PPh 3 O (Ph = C 6 H 5). It is one of the more common phosphine oxides. This colourless crystalline compound is a common but potentially useful waste product in reactions involving triphenylphosphine.
Tetrakis(triphenylphosphine)palladium(0) is widely used to catalyse C-C coupling reactions in organic synthesis, see Heck reaction. Wilkinson's catalyst , RhCl(PPh 3 ) 3 is a square planar Rh(I) complex of historical significance used to catalyze the hydrogenation of alkenes.
The reagent is prepared from the chloromethylphosphonium salt [Ph 3 PCH 2 Cl]Cl by treatment with strong base. The phosphonium compound is generated by treatment of triphenylphosphine with chloroiodomethane. [1] (Chloromethylene)triphenylphosphorane converts aldehydes to vinyl chlorides: RCHO + Ph 3 P=CHCl → RCH=CHCl + Ph 3 PO
The methylation of triphenylphosphine is the first step in the preparation of the Wittig reagent. Illustrative phosphorus(V) compounds: the phosphonium ion P(CH 2 OH) 4 +, two resonance structures for the Wittig reagent Ph 3 PCH 2, and pentaphenylphosphorane, a rare pentaorganophophorus compound. The parent phosphorane (σ 5 λ 5) is PH 5 ...
First phosphine imine-forming reaction is conducted involving treatment of the azide with the phosphine. The intermediate, e.g. triphenylphosphine phenylimide, is then subjected to hydrolysis to produce a phosphine oxide and an amine: R 3 P=NR' + H 2 O → R 3 P=O + R'NH 2. The overall conversion is a mild method of reducing an azide to an amine.
Less basic phosphines, such as methyldiphenylphosphine are converted to their oxides by treatment with hydrogen peroxide: [8] PMePh 2 + H 2 O 2 → OPMePh 2 + H 2 O. Phosphine oxides are generated as a by-product of the Wittig reaction: R 3 PCR' 2 + R" 2 CO → R 3 PO + R' 2 C=CR" 2