Triphenyl phosphite

Triphenyl phosphite is the chemical compound with the formula P(OC₆H₅)₃. This colourless viscous liquid is the ester of phosphorous acid and phenol. It is used as a ligand in organometallic chemistry. Nickel complexes of this ligand are homogeneous catalysts for the hydrocyanation of alkenes.

Additional recommended knowledge

What is the Correct Way to Check Repeatability in Balances?

Don't let static charges disrupt your weighing accuracy

Correct Test Weight Handling Guide: 12 Practical Tips

Triphenylphosphite is prepared from phosphorus trichloride and phenol in the presence of a base:

PCl₃ + 3 HOC₆H₅ → P(OC₆H₅)₃ + 3 HCl

Trimethylphosphine is prepared from triphenylphosphite:^[1]

3 CH₃MgBr + P(OC₆H₅)₃ → P(CH₃)₃ + 3 MgBrOC₆H₅

Representative coordination complexes

Triphenylphosphite forms zero-valent complexes of the type M[P(OC₆H₅)₃]₄ for M = Ni, Pd, Pt. The colourless nickel complex (m.p. 147 °C) can be prepared from the nickel(0) complex of 1,5-cyclooctadiene:^[2]

Ni(COD)₂ + 4 P(OC₆H₅)₃ → Ni[P(OC₆H₅)₃]₄ + 2 COD

It also forms a variety of Fe(O) and Fe(II) complexes such as the dihydride H₂Fe[P(OC₆H₅)₃]₄.^[3]

References

1. ^ Leutkens, Jr., M. L.; Sattelberger, A. P.; Murray, H. H.; Basil, J. D.; Fackler, Jr., J. P. "Trimethylphosphine" Inorganic Syntheses, 1990, volume 28, pages 305-310. ISBN 0-471-52619-3
2. ^ Ittel, S. D. "Olefin, Acetylene, Phosphine, Isocyanide, and Diazene Complexes of Nickel(0)" Inorganic Syntheses, 1977, volume XVII, p. 117-124. ISBN 0-07-044327-0,
3. ^ Gerlach, D. H.; Peet, W. G. and Muetterties, E. L., "Stereochemically nonrigid six-coordinate molecules. II. Preparations and reactions of tetrakis(organophosphorus)metal dihydride complexes", Journal of the American Chemical Societry, 1972, volume 94, pp 4545-9.DOI: 10.1021/ja00768a022