1,2-Bis(diphenylphosphino)ethane
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Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox headerbarTemplate:Chembox GHS (set)Template:Chembox Datapage checkTemplate:Chembox Footer| Template:Longitem | Template:Unbulleted list |
| Template:Longitem | 761261 |
| ChEBI | Template:Unbulleted list |
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| Template:Longitem | 9052 |
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| Template:Longitem | C26H24P2 |
| Molar mass | 398.42 g/mol |
| Melting point | Template:Chembox CalcTemperatures |
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1,2-Bis(diphenylphosphino)ethane (dppe) is an organophosphorus compound with the formula (Ph2PCH2)2 (Ph = phenyl). It is a common symmetrical bidentate ligand in coordination chemistry. It is a white solid that is soluble in organic solvents.
Preparation
The preparation of dppe entails the alkylation of NaP(C6H5)2 with 1,2-dichloroethane:[1][2]
Reactions
The reduction of dppe by lithium give the disecondary phosphine:[3]
Hydrolysis gives the bis(secondary phosphine).
- Template:Chem2
File:HFeCl dppe 2.svg The bis(dppe) complex HFeCl(dppe)2 is one of the most accessible transition metal hydrides.
Treatment of dppe with hydrogen peroxide produces the phosphine oxides Template:Chem2.[4] Selective mono-oxidation of dppe can be achieved by benzylation followed by hydrolysis:
Hydrogenation of dppe gives the ligand bis(dicyclohexylphosphino)ethane.
Coordination complexes
Many coordination complexes of dppe are known, and some are used as homogeneous catalysts. Dppe is almost invariably chelating, although there are examples of monodentate (e.g., W(CO)5(dppe)) and of bridging behavior.[5] The natural bite angle is 86°.[6]
Related compounds
References
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- ↑ Script error: No such module "Citation/CS1".
- ↑ Girolami, G.; Rauchfuss, T.; Angelici, R. Synthesis and Technique in Inorganic Chemistry, 3rd ed.; University Science Books: Sausalito, CA, 1999; pp. 85-92. Template:ISBN
- ↑ Script error: No such module "Citation/CS1".
- ↑ Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley & Sons, Ltd
- ↑ Cotton, F.A.; Wilkinson, G. Advanced Inorganic Chemistry: A Comprehensive Text, 4th ed.; Wiley-Interscience Publications: New York, NY, 1980; p.246. Template:ISBN
- ↑ Script error: No such module "Citation/CS1".
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