Xantphos
From Wikipedia, the free encyclopedia
| Xantphos | |
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| IUPAC name | 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene |
| Other names | Xantphos |
| Identifiers | |
| CAS number | [161265-03-8] |
| PubChem | |
| Properties | |
| Molecular formula | C39H32OP2 |
| Molar mass | 578.62 g/mol |
| Appearance | colourless solid |
| Density | 1.34 g/mL |
| Melting point |
224-228 °C |
| Solubility in water | organic solvents |
| Hazards | |
| Main hazards | flammable |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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 ilithiation of 9,9-dimethylxanthene with sec-butyllithium followed by treatment with chlorodiphenylphosphine.[2]
[edit] References
- ^ 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: 2741–2769. doi:.
- ^ 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: 3081–3089. doi:.
