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Triphenylarsine

Triphenylarsine

Triphenylborane

Triphenylphosphine

Triphenylstibine Triphenylarsine is the chemical compound with the formula As(C6H5)3. This organoarsenic compound, often abbreviated AsPh3, is a colorless crystalline solid that is used as a ligand and a reagent in coordination chemistry and organic synthesis. The molecule is pyramidal with As-C distances of 1.942–1.956 Å and C-As-C angles of 99.6–100.5°.

Preparation

Triphenylarsine is prepared by treating phenyl lithium with arsenic tribromide. The method can be used to prepare many analogues with diverse aryl groups.

Triphenylarsine can also be prepared by the Wurtz-like reaction of arsenic trichloride with chlorobenzene using sodium as the reducing agent: :AsCl3 + 3 PhCl + 6 Na → AsPh3 + 6 NaCl

Reactions

Reaction of triphenylarsine with lithium gives lithium diphenylarsenide and phenyllithium: :AsPh3 + 2 Li → LiAsPh2 + LiPh

Triphenylarsine is the precursor to tetraphenylarsonium chloride, [AsPh4]Cl, a popular precipitating agent.

Many metal-arsine complexes have been prepared using AsPh3. Examples include IrCl(CO)(AsPh3)2, RhCl(AsPh3)3, and Fe(CO)4(AsPh3).

Treatment of triphenylarsine with hydrogen peroxide gives triphenylarsine oxide: :

References

References

  1. Mazhar-ul-Haque, Hasan A. Tayim, Jamil Ahmed, and William Horne "Crystal and molecular structure of triphenylarsine" ''Journal of Chemical Crystallography'' Volume 15, Number 6 / 1985. {{doi. 10.1007/BF01164771
  2. (2020). "Fundamental Study on Arsenic(III) Halides (AsX3; X = Br, I) toward the Construction of ''C''3-Symmetrical Monodentate Arsenic Ligands". Inorganic Chemistry.
  3. W. Levason. (1976). "cis-2-Diphenylarsinovinyldiphenylphosphine and 2-Diphenylarsinoethyldiphenylphosphine".
  4. (1950). "Tetraphenylarsonium Chloride Hydrochloride". Organic Syntheses.
  5. (1973). "Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands". J. Wiley.
  6. (2015). "Encyclopedia of Reagents for Organic Synthesis".
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