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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 chemistry.
The main limitation of the traditional Wittig reaction is that the reaction proceeds mainly via the erythro betaine intermediate, which leads to the Z-alkene. The erythro betaine can be converted to the threo betaine using phenyllithium at low temperature. [18] This modification affords the E-alkene. The Schlosser variant of the Wittig reaction
Triphenylphosphine oxide can be difficult to remove from reaction mixtures by means of chromatography. It is poorly soluble in hexane and cold diethyl ether . Trituration or chromatography of crude products with these solvents often leads to a good separation of triphenylphosphine oxide.
One of the first applications of phosphine ligands in catalysis was the use of triphenylphosphine in "Reppe" chemistry (1948), which included reactions of alkynes, carbon monoxide, and alcohols. [16] In his studies, Reppe discovered that this reaction more efficiently produced acrylic esters using NiBr 2 (PPh 3) 2 as a catalyst instead of NiBr 2.
The reaction mechanism of the Mitsunobu reaction is fairly complex. The identity of intermediates and the roles they play has been the subject of debate. Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5.
The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. [1] [2] The reaction was discovered by and named after Hermann Staudinger. [3] The reaction follows this stoichiometry: R 3 P + R'N 3 → R 3 P=NR' + N 2
Reactions. Triphenylphosphite is a precursor to trimethylphosphine, it serves as a source of P 3+ that is less electrophilic than phosphorus trichloride: [1]
The Appel reaction is an organic reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride. [1] The use of carbon tetrabromide or bromine as a halide source will yield alkyl bromides, whereas using carbon tetraiodide , methyl iodide or iodine gives alkyl iodides .