1,3-Bis(diphenylphosphino)propane

477204968 Dppp.svg 200px Dppp-from-xtal-2005-3D-balls.png (Propane-1,3-diyl)bis(diphenylphosphane) DPPP correct chemspider 73276 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 LVEYOSJUKRVCCF-UHFFFAOYAP c1ccc(cc1)P(CCCP(c2ccccc2)c3ccccc3)c4ccccc4 correct EBI 73394 correct chemspider 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 correct chemspider LVEYOSJUKRVCCF-UHFFFAOYSA-N correct CAS 6737-42-4 correct FDA 44R56E2C68 81219 P(c1ccccc1)(c2ccccc2)CCCP(c3ccccc3)c4ccccc4 27 26 2 white solid chlorocarbons 1,3-Bis(diphenylphosphino)propane (dppp) is an organophosphorus compound with the formula Ph2P(CH2)3PPh2. 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 + Cl(CH2)3Cl → Ph2P(CH2)3PPh2 + 2 LiCl However, it can be synthesised via a much more controllable (and cheaper) route, via metal-halogen exchange and then metathesis: Br(CH2)3Br + 2 tBuLi → Li(CH2)3Li + 2 tBuBr Li(CH2)3Li + 2 PCl3 → Cl2P(CH2)3PCl2 + 2 LiCl Cl2P(CH2)3PCl2 + 4 PhLi → Ph2P(CH2)3PPh2 + 4 LiCl Coordination chemistry and use as co-catalyst The diphosphine serves as a bidentate ligand forming six-membered C3P2M chelate ring with a natural bite angle of 91°.Birkholz (née Gensow) Mandy-Nicole Freixa Zoraida van Leeuwen Piet W. N. M. Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions Chemical Society Reviews 2009 38 4 1099–1118 10.1039/B806211K 19421583 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. Kumada, Makota Tamao, Kohei Sumitani, Koji Phosphine-Nickel Complex Catalyzed Cross-Coupling of Grignard Reagents with Aryl and Alkenyl Halides: 1,2-dibutylbenzene 6 407 1988 cv6p0407 Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones. 10.1002/0471440264.pst273 Encyclopedia Of Polymer Science and Technology Polyketones 2001 Drent E. Mul W. P. Smaardijk A. A. 9781118633892 Dppp can sometimes be used in palladium-catalyzed arylation under Heck reaction conditions to control regioselectivity.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. 10.1021/jo00031a029 References Category:Diphosphines Category:Phenyl compounds