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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).
For example, lithium diphenylphosphide is readily methylated with methyl iodide to give methyldiphenylphosphine: LiiP(C 6 H 5) 2 + CH 3 I → CH 3 P(C 6 H 5) 2 + LiI. Phosphine is a precursor to some tertiary phosphines by hydrophosphination of alkenes. For example, in the presence of basic catalysts PH 3 adds of Michael acceptors such as ...
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
General formula of organophosphine oxides. Phosphine oxides are phosphorus compounds with the formula OPX 3. When X = alkyl or aryl, these are organophosphine oxides. Triphenylphosphine oxide is an example. An inorganic phosphine oxide is phosphoryl chloride (POCl 3). [1] The parent phosphine oxide (H 3 PO) remains rare and obscure.
A metal-phosphine complex is a coordination complex containing one or more phosphine ligands. Almost always, the phosphine is an organophosphine of the type R 3 P (R = alkyl, aryl). Metal phosphine complexes are useful in homogeneous catalysis .
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.
Two P-chiral "Kwon phosphines". [1]P-Chiral phosphines are organophosphorus compounds of the formula PRR′R″, where R, R′, R″ = H, alkyl, aryl, etc. They are a subset of chiral phosphines, a broader class of compounds where the stereogenic center can reside at sites other than phosphorus.
For example, the reaction of triphenylphosphine with methyl bromide gives methyltriphenylphosphonium bromide: PPh 3 + CH 3 Br → [CH 3 PPh 3] + Br −. The methyl group in such phosphonium salts is mildly acidic, with a pK a estimated to be near 15: [5] [CH 3 PPh 3] + + base → CH 2 =PPh 3 + [Hbase] + This deprotonation reaction gives Wittig ...