triphenylphosphine
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. 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. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.
Article
17 sectionsContents
- Preparation and structure
- Principal reactions with chalcogens, halogens, and acids
- Oxidation
- Chlorination
- Protonation
- Organic reactions
- Quaternization
- Mitsunobu reaction
- Appel reaction
- Deoxygenation
- Sulfonation
- Reduction to diphenylphosphide
- Transition metal complexes
- Polymer-anchored PPh<sub>3</sub> derivatives
- See also
- References
- External links
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. 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. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.
==Preparation and structure== Triphenylphosphine can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium. The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium: PCl3 + 3 PhCl + 6 Na → PPh3 + 6 NaCl