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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 ...
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 .
The nature of the P–O bond was once hotly debated. Some discussions invoked a role for phosphorus-centered d-orbitals in bonding, but this analysis is not supported by computational analyses. In terms of simple Lewis structure, the bond is more accurately represented as a dative bond, as is currently used to depict an amine oxide. [3] [4]
The P-O distance elongates by ca. 2%. In triphenylphosphine oxide, the P-O distance is 1.48 Å. [3] In NiCl 2 [OP(C 6 H 5) 3] 2, the distance is 1.51 Å (see figure). A similar elongation of the P-O bond is seen in cis-WCl 4 (OPPh 3) 2. [4] The trend is consistent with the stabilization of the ionic resonance structure upon complexation.
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 ...
Chemical formula. C 18 H 15 O 3 P Molar mass: 310.28 g/mol Appearance colourless liquid Density: 1.184 g/mL Melting point: 22 to 24 °C (72 to 75 °F; 295 to 297 K)
Triphenylphosphine dichloride, (C 6 H 5) 3 PCl 2, is a chlorinating agent widely used in organic chemistry. Applications include the conversion of alcohols and ethers to alkyl chlorides , the cleavage of epoxides to vicinal dichlorides and the chlorination of carboxylic acids to acyl chlorides .
Triphenylphosphine sulfide (IUPAC name: triphenyl-λ 5-phosphanethione) is the organophosphorus compound with the formula (C 6 H 5) 3 PS, usually written Ph 3 PS (where Ph = phenyl). It is a colourless solid, which is soluble in a variety of organic solvents.