1,2-Bis(diphenylphosphino)ethane

changed 477203175 1,2-Bis(diphenylphosphino)ethane DPPE structure.svg skin-invert-image Dppe-from-xtal-2001-3D-balls.png bg-transparent dppe (Ethane-1,2-diyl)bis(diphenylphosphane) 1,2-Bis(diphenylphosphino)ethaneDiphosDppe correct chemspider correct EBI 30669 66873 74267 216-769-2 KL33QE52I4 1/C26H24P2/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/h1-20H,21-22H2 P(c1ccccc1)(c2ccccc2)CCP(c3ccccc3)c4ccccc4 QFMZQPDHXULLKC-UHFFFAOYAX c1ccc(cc1)P(CCP(c2ccccc2)c3ccccc3)c4ccccc4 correct EBI 68683 761261 9052 correct chemspider 1S/C26H24P2/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/h1-20H,21-22H2 correct chemspider QFMZQPDHXULLKC-UHFFFAOYSA-N correct CAS 1663-45-2 C26H24P2 398.42 g/mol 140 to 142 07 09 Warning 302 315 319 332 335 410 261 264 270 271 273 280 301+312 302+352 304+312 304+340 305+351+338 312 321 330 332+313 337+313 362 391 403+233 405 501 1,2-Bis(diphenylphosphino)ethane (dppe) is an organophosphorus compound with the formula (Ph2PCH2)2 (Ph = phenyl). It is a common symmetrical bidentate ligand in coordination chemistry. It is a white solid that is soluble in organic solvents. Preparation The preparation of dppe entails the alkylation of NaP(C6H5)2 with 1,2-dichloroethane: J. Chem. Soc. 1962 1490–1494 10.1039/JR9620001490 283. The preparation of di- and tri-tertiary phosphines W. Hewertson and H. R. WatsonGirolami, G.; Rauchfuss, T.; Angelici, R. Synthesis and Technique in Inorganic Chemistry, 3rd ed.; University Science Books: Sausalito, CA, 1999; pp. 85-92. 0-935702-48-2 2 NaP(C6H5)2 + ClCH2CH2Cl -> (C6H5)2PCH2CH2P(C6H5)2 + 2 NaCl Reactions The reduction of dppe by lithium gives the disecondary phosphine: Dogan, J. Schulte, J.B. Swiegers, G.F. Wild, S.B. 2000 Mechanism of Phosphorus-Carbon Bond Cleavage by Lithium in Tertiary Phosphines. An Optimized Synthesis of 1, 2-Bis (phenylphosphino) ethane J. Org. Chem. 65 4 951–957 10.1021/jo9907336 10814038 (C6H5)2PCH2CH2P(C6H5)2 4 Li -> Li(C6H5)PCH2CH2P(C6H5)Li + 2 C6H5Li Hydrolysis gives the bis(secondary phosphine). Li(C6H5)PCH2CH2P(C6H5)Li + 2 H2O -> H(C6H5)PCH2CH2P(C6H5)H + 2 LiOH thumb|class=skin-invert-image|left|The bis(dppe) complex HFeCl(dppe)2 is one of the most accessible transition metal hydrides. Treatment of dppe with hydrogen peroxide produces the phosphine oxides (C6H5)2P(O)CH2CH2P(C6H5)2 and (C6H5)2P(O)CH2CH2P(O)(C6H5)2.Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley & Sons, Ltd Selective mono-oxidation of dppe can be achieved by benzylation followed by hydrolysis: (C6H5)2PCH2CH2P(C6H5)2 + C6H5CH2Br -> (C6H5)2PCH2CH2P(C6H5)2(CH2C6H5)]Br (C6H5)2PCH2CH2P(C6H5)2(CH2C6H5)]Br + NaOH -> (C6H5)2PCH2CH2P(O)(C6H5)2 + C6H5CH3 + NaBr Hydrogenation of dppe gives the ligand bis(dicyclohexylphosphino)ethane. Coordination complexes Many coordination complexes of dppe are known, and some are used as homogeneous catalysts. Dppe is almost invariably chelating, although there are examples of monodentate (e.g., W(CO)5(dppe)) and of bridging behavior.Cotton, F.A.; Wilkinson, G. Advanced Inorganic Chemistry: A Comprehensive Text, 4th ed.; Wiley-Interscience Publications: New York, NY, 1980; p.246. 0-471-02775-8 The natural bite angle is 86°.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 Related compounds 1,2-Bis(dimethylphosphino)ethane Bis(diphenylphosphino)methane References Category:Chelating agents Category:Diphosphines Category:Phenyl compounds Category:1,2-Ethanediyl compounds