Xantphos

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Xantphos
Xantphos.png
Xantphos-3D-balls.png
Names
IUPAC name
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
Other names
Xantphos
Identifiers
161265-03-8 N
ChemSpider 551930 YesY
Jmol 3D model Interactive image
PubChem 636044
Properties
C39H32OP2
Molar mass 578.62 g/mol
Appearance colorless solid
Density 1.34 g/mL
Melting point 224 to 228 °C (435 to 442 °F; 497 to 501 K)
organic solvents
Hazards
Main hazards flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references
Not to be confused with XPhos.

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[edit]

  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.