| 1,2-Bis(diphenylphosphino)ethane | |
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Ethane-1,2-diylbis(diphenylphosphane) |
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Other names
1,2-Bis(diphenylphosphino)ethane |
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| Identifiers | |
| CAS number | 1663-45-2 |
| ChemSpider | 66873 |
| ChEBI | CHEBI:30669 |
| ChEMBL | CHEMBL68683 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C26H24P2 |
| Molar mass | 398.42 g/mol |
| Melting point |
140-142 °C |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
1,2-Bis(diphenylphosphino)ethane (dppe) is a commonly used bidentate ligand in coordination chemistry. Dppe is almost invariably chelated, although there are examples of unidentate (e.g., W(CO)5(dppe)) and of bridging behavior.[1]
Contents |
The preparation of dppe is conducted via the alkylation of NaPPh2 which is typically prepared from triphenylphosphine (P(C6H5)3) as follows:[2][3]
NaP(C6H5)2, which is readily air-oxidized, is treated with 1,2-dichloroethane (ClCH2CH2Cl) to give dppe:
The reduction of dppe by lithium to give PhHP(CH2)2PHPh has been reported.[4]
Hydrolysis by water gives:
Treatment of dppe with conventional oxidants such as hydrogen peroxide (H2O2), aqueous bromine (Br2), etc., always produces dppeO in low yield (e.g., 13%) as a result of non-selective oxidation leading to mixtures of the starting material, the monoxide, and dioxide.[5] Selective mono-oxidation of dppe can be achieved by reaction with PhCH2Br to give dppeO.
This is followed by purification and alkaline catalyzed hydrolysis of the mono-phosphonium salt.
Coordination complexes of dppe, and diphosphine ligands in general, are almost entirely used as homogeneous catalysts for a wide range of reactions. Two simple coordination complexes of dppe include Pd(dppe)2 and Ir(dppe)2. Pd(dppe)2 can be prepared by reduction of Pd(II) with NaBH4. It is most conveniently prepared, however, in situ from Pd(OAc)2.[5]