1,3-Bis(diphenylphosphino)propane

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1,3-Bis(diphenylphosphino)propane
Dppp.svg
Dppp-from-xtal-2005-3D-balls.png
Names
IUPAC name
Propane-1,3-diylbis(diphenylphosphane)
Identifiers
6737-42-4 YesY
Abbreviations DPPP
ChEMBL ChEMBL73394 YesY
ChemSpider 73276 YesY
Jmol 3D model Interactive image
Interactive image
PubChem 81219
  • InChI=1S/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2 YesY
    Key: LVEYOSJUKRVCCF-UHFFFAOYSA-N YesY
  • InChI=1/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2
    Key: LVEYOSJUKRVCCF-UHFFFAOYAP
  • P(c1ccccc1)(c2ccccc2)CCCP(c3ccccc3)c4ccccc4
  • c1ccc(cc1)P(CCCP(c2ccccc2)c3ccccc3)c4ccccc4
Properties
C27H26P2
Molar mass 412.45 g·mol−1
Appearance white solid
chlorocarbons
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

1,3-Bis(diphenylphosphino)propane (dppp) is an organophosphorus compound with the formula (CH2)3(P(C6H5)2)2. The compound is a white solid that is soluble in organic solvents. It is slightly air-sensitive, degrading in air to the phosphine oxide. It is classified as a diphosphine ligand in coordination chemistry and homogeneous catalysis.

The diphosphine can be prepared by the reaction of lithium diphenylphosphide and 1,3-dichloropropane (Ph = C6H5):

2 Ph2PLi + C3H6Cl2 → C3H6(PPh2)2 + 2 LiCl

Coordination chemistry and use as co-catalyst

The diphosphine serves as a bidentate ligand forming six-membered C3P2M chelate ring. For example, the complex dichloro(1,3-bis(diphenylphosphino)propane)nickel is prepared by combining equimolar portions of the ligand and nickel(II) chloride hexahydrate. This nickel complex serves as a catalyst for the Kumada coupling reaction.[1] Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones.[2] Dppp can sometimes be used in palladium-catalyzed arylation under Heck reaction conditions to control regioselectivity.[3]

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Cabri, Walter; Candiani, Ilaria; Bedeschi Angelo; Penco, Sergio"α-Regioselectivity in Palladium-Catalyzed Arylation of Acyclic Enol Ethers" journal= Journal of Organic Chemistry, 1991, volume 57, p. 1481. doi:10.1021/jo00031a029
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