cis-1,2-Bis(diphenylphosphino)ethylene (dppv) is an organophosphorus compound with the formula C2H2(PPh2)2 (Ph = C6H5). Both the cis and trans isomers are known, but the cis isomer is of primary interest. Classified as a diphosphine ligand, it is a bidentate ligand in coordination chemistry. For example it gives rise to the complex Ni(dppv)2 and the coordination polymer [Ni(dppv)]n.[1] As a chelating ligand, dppv is very similar to 1,2-bis(diphenylphosphino)benzene.
ethylene.svg) cis isomer
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| Names | |
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| IUPAC name
1,1'-(1Z)-1,2-ethenediylbis[1,1-diphenylphosphine
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.012.336 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C26H22P2 | |
| Molar mass | 396.410 g·mol−1 |
| Appearance | white solid |
| Melting point | 125 °C (257 °F; 398 K) |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The diphosphine is prepared by reaction of lithium diphenylphosphide with cis-dichloroethylene.[2]
- 2 LiPPh2 + C2H2Cl2 → C2H2(PPh2)2 + 2 LiCl
trans-1,2-Bis(diphenylphosphino)ethylene is made similarly, but using trans-dichloroethylene.
References
edit- ^ Proft, Bernd; Pörschke, Klaus-Richard (1993). "Cis-1,2-Bis(diphenylphosphino)ethen-Nickel(0)-Komplexe / Cis-1,2-Bis(diphenylphosphino)ethene Nickel(0) Complexes". Zeitschrift für Naturforschung B. 48 (7): 919–927. doi:10.1515/znb-1993-0712. S2CID 98395128.
- ^ Aguiar, Adam M.; Daigle, Donald. (1964). "A Stereospecific Route to trans- and cis-1,2-Vinylenebis(diphenylphosphine)". Journal of the American Chemical Society. 86 (11): 2299–2300. doi:10.1021/ja01065a049.