{{chembox |verifiedrevid = 477204968 |ImageFile=Dppp.svg |ImageSize=200px |ImageFile1=Dppp-from-xtal-2005-3D-balls.png |PIN=(Propane-1,3-diyl)bis(diphenylphosphane) |Section1={{Chembox Identifiers |Abbreviations = DPPP |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID = 73276 |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 |InChIKey = LVEYOSJUKRVCCF-UHFFFAOYAP |SMILES1 = c1ccc(cc1)P(CCCP(c2ccccc2)c3ccccc3)c4ccccc4 |ChEMBL_Ref = {{ebicite|correct|EBI}} |ChEMBL = 73394 |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI = 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 |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey = LVEYOSJUKRVCCF-UHFFFAOYSA-N |CASNo_Ref = {{cascite|correct|CAS}} |CASNo=6737-42-4 |UNII_Ref = {{fdacite|correct|FDA}} |UNII = 44R56E2C68 |PubChem=81219 |SMILES = P(c1ccccc1)(c2ccccc2)CCCP(c3ccccc3)c4ccccc4 }} |Section2={{Chembox Properties |C=27 | H=26 | P=2 |Appearance= white solid |Solubility= chlorocarbons }} }}
'''1,3-Bis(diphenylphosphino)propane''' ('''dppp''') is an organophosphorus compound with the formula Ph{{sub|2}}P(CH{{sub|2}}){{sub|3}}PPh{{sub|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 = C{{sub|6}}H{{sub|5}}): : 2 Ph{{sub|2}}PLi + Cl(CH{{sub|2}}){{sub|3}}Cl → Ph{{sub|2}}P(CH{{sub|2}}){{sub|3}}PPh{{sub|2}} + 2 LiCl
However, it can be synthesised via a much more controllable (and cheaper) route, via metal-halogen exchange and then metathesis: :Br(CH{{sub|2}}){{sub|3}}Br + 2 {{sup|t}}BuLi → Li(CH{{sub|2}}){{sub|3}}Li + 2 {{sup|t}}BuBr :Li(CH{{sub|2}}){{sub|3}}Li + 2 PCl{{sub|3}} → Cl{{sub|2}}P(CH{{sub|2}}){{sub|3}}PCl{{sub|2}} + 2 LiCl :Cl{{sub|2}}P(CH{{sub|2}}){{sub|3}}PCl{{sub|2}} + 4 PhLi → Ph{{sub|2}}P(CH{{sub|2}}){{sub|3}}PPh{{sub|2}} + 4 LiCl
==Coordination chemistry and use as co-catalyst== The diphosphine serves as a bidentate ligand forming six-membered C{{sub|3}}P{{sub|2}}M chelate ring with a natural bite angle of 91°.<ref name="vanLeeuwen">{{cite journal |last1=Birkholz (née Gensow) |first1=Mandy-Nicole |last2=Freixa |first2=Zoraida |last3=van Leeuwen |first3=Piet W. N. M. |title=Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions |journal=Chemical Society Reviews |date=2009 |volume=38 |issue=4 |pages=1099–1118 |doi=10.1039/B806211K |pmid=19421583}}</ref> 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.<ref name = kumada>{{OrgSynth | author = Kumada, Makota | author2 = Tamao, Kohei | author3 = Sumitani, Koji | title = Phosphine-Nickel Complex Catalyzed Cross-Coupling of Grignard Reagents with Aryl and Alkenyl Halides: 1,2-dibutylbenzene | collvol = 6 | collvolpages = 407 | year = 1988 | prep = cv6p0407}}</ref> Dppp is also used as a ligand for palladium(II) catalysts to co-polymerize carbon monoxide and ethylene to give polyketones.<ref>{{cite encyclopedia | doi = 10.1002/0471440264.pst273 | encyclopedia = Encyclopedia Of Polymer Science and Technology | title = Polyketones | year = 2001 | last1 = Drent | first1 = E. | last2 = Mul | first2 = W. P. | last3 = Smaardijk | first3 = A. A.| isbn = 9781118633892 }}</ref> Dppp can sometimes be used in palladium-catalyzed arylation under Heck reaction conditions to control regioselectivity.<ref>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}}</ref>
==References== {{Reflist}}
{{DEFAULTSORT:Bis(diphenylphosphino)propane, 1, 3-}} Category:Diphosphines Category:Phenyl compounds