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1,2-Bis(diphenylphosphino)ethylene

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1,2-Bis(diphenylphosphino)ethylene

cis isomer
Names
IUPAC name 1,1'-(1Z)-1,2-ethenediylbis[1,1-diphenylphosphine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.012.336 Edit this at Wikidata
EC Number
  • 213-569-7
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C26H22P2/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-22H/b22-21-Key: NCKJIJSEWKIXAT-DQRAZIAOSA-N
SMILES
  • C1=CC=C(C=C1)P(/C=C\P(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
Properties
Chemical formula C26H22P2
Molar mass 396.410 g·mol
Appearance white solid
Melting point 125 °C (257 °F; 398 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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 n. As a chelating ligand, dppv is very similar to 1,2-bis(diphenylphosphino)benzene.

The diphosphine is prepared by reaction of lithium diphenylphosphide with cis-dichloroethylene.

2 LiPPh2 + C2H2Cl2 → C2H2(PPh2)2 + 2 LiCl

trans-1,2-Bis(diphenylphosphino)ethylene is made similarly, but using trans-dichloroethylene.

References

  1. 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.
  2. 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.
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