Xantphos

Xantphos
IUPAC name

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
Other names

Xantphos
Identifiers
CAS number 161265-03-8 Y
PubChem 636044
ChemSpider 551930 Y
Jmol-3D images Image 1
Properties
Molecular formula C39H32OP2
Molar mass 578.62 g/mol
Appearance colorless solid
Density 1.34 g/mL
Melting point

224-228 °C, 497-501 K, 435-442 °F
Solubility in water organic solvents
Hazards
Main hazards flammable
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Xantphos is an organophosphorus compound derived from the heterocycle xanthene. It is used as a bidentate ligand and is noteworthy for having a particularly wide bite angle. Such ligands are useful in the hydroformylation of alkenes.[1] Illustrative of its wide bite angle, it forms both cis and trans adducts of platinum(II) chloride. A related bidentate ligand with a greater bite angle is spanphos.

The ligand is prepared by double directed lithiation of 9,9-dimethylxanthene with sec-butyllithium followed by treatment with chlorodiphenylphosphine.[2]

References

  1. ^ Piet W. N. M. van Leeuwen, Paul C. J. Kamer, Joost N. H. Reek, and Peter Dierkes (2000). "Ligand Bite Angle Effects in Metal-catalyzed C-C Bond Formation". Chemical Reviews 100 (8): 2741–2769. doi:10.1021/cr9902704. PMID 11749304. 
  2. ^ Mirko Kranenburg, Yuri E. M. van der Burgt, Paul C. J. Kamer, Piet W. N. M. van Leeuwen, Kees Goubitz, and Jan Fraanje (1995). "New Diphosphine Ligands Based on Heterocyclic Aromatics Inducing Very High Regioselectivity in Rhodium-Catalyzed Hydroformylation: Effect of the Bite Angle". Organometallics 14 (6): 3081–3089. doi:10.1021/om00006a057.