The bis(dppe) complex HFeCl(dppe)2 is one of the most accessible transition metal hydrides.
Treatment of dppe with conventional oxidants such as hydrogen peroxide (H2O2), aqueous bromine (Br2), etc., produces dppeO in low yield (e.g., 13%) as a result of non-selective oxidation.[4] Selective mono-oxidation of dppe can be achieved by reaction with PhCH2Br to give dppeO.
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.[5] The natural bite angle is 86°.[6]
^W. Hewertson and H. R. Watson (1962). "283. The preparation of di- and tri-tertiary phosphines". J. Chem. Soc.: 1490–1494. doi:10.1039/JR9620001490.
^Girolami, G.; Rauchfuss, T.; Angelici, R. Synthesis and Technique in Inorganic Chemistry, 3rd ed.; University Science Books: Sausalito, CA, 1999; pp. 85-92. ISBN0-935702-48-2
^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. doi:10.1021/jo9907336. PMID 10814038.
^Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley & Sons, Ltd
^Cotton, F.A.; Wilkinson, G. Advanced Inorganic Chemistry: A Comprehensive Text, 4th ed.; Wiley-Interscience Publications: New York, NY, 1980; p.246. ISBN0-471-02775-8
^Birkholz (née Gensow), Mandy-Nicole; Freixa, Zoraida; van Leeuwen, Piet W. N. M. (2009). "Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions". Chemical Society Reviews. 38 (4): 1099–1118. doi:10.1039/B806211K. PMID 19421583.
December 15, 2023
diphenylphosphino, ethane, dppe, organophosphorus, compound, with, formula, ph2pch2, phenyl, commonly, used, bidentate, ligand, coordination, chemistry, white, solid, that, soluble, organic, solvents, namespreferred, iupac, name, ethane, diyl, diphenylphosphan. 1 2 Bis diphenylphosphino ethane dppe is an organophosphorus compound with the formula Ph2PCH2 2 Ph phenyl It is a commonly used bidentate ligand in coordination chemistry It is a white solid that is soluble in organic solvents 1 2 Bis diphenylphosphino ethane NamesPreferred IUPAC name Ethane 1 2 diyl bis diphenylphosphane Other names 1 2 Bis diphenylphosphino ethaneDiphosDppeIdentifiersCAS Number 1663 45 2 Y3D model JSmol Interactive imageInteractive imageBeilstein Reference 761261ChEBI CHEBI 30669 YChEMBL ChEMBL68683 YChemSpider 66873 YECHA InfoCard 100 015 246EC Number 216 769 2Gmelin Reference 9052PubChem CID 74267UNII KL33QE52I4CompTox Dashboard EPA DTXSID2061858InChI InChI 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 YKey QFMZQPDHXULLKC UHFFFAOYSA N YInChI 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 22H2Key QFMZQPDHXULLKC UHFFFAOYAXSMILES P c1ccccc1 c2ccccc2 CCP c3ccccc3 c4ccccc4c1ccc cc1 P CCP c2ccccc2 c3ccccc3 c4ccccc4PropertiesChemical formula C26H24P2Molar mass 398 42 g molMelting point 140 to 142 C 284 to 288 F 413 to 415 K HazardsGHS labelling PictogramsSignal word WarningHazard statements H302 H315 H319 H332 H335 H410Precautionary statements P261 P264 P270 P271 P273 P280 P301 P312 P302 P352 P304 P312 P304 P340 P305 P351 P338 P312 P321 P330 P332 P313 P337 P313 P362 P391 P403 P233 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Preparation 2 Reactions 3 Coordination complexes 4 Related compounds 5 ReferencesPreparation editThe preparation of dppe is by the alkylation of NaPPh2 1 2 P C6H5 3 2 Na NaP C6H5 2 NaC6H5NaP C6H5 2 which is readily air oxidized is treated with 1 2 dichloroethane ClCH2CH2Cl to give dppe 2 NaP C6H5 2 ClCH2CH2Cl C6H5 2PCH2CH2P C6H5 2 2 NaClReactions editThe reduction of dppe by lithium to give PhHP CH2 2PHPh has been reported 3 Ph2P CH2 2PPh2 4 Li PhLiP CH2 2PLiPh 2 PhLiHydrolysis gives the bis secondary phosphine PhLiP CH2 2PLiPh 2 PhLi 4H2O PhHP CH2 2PHPh 4 LiOH 2 C6H6 nbsp The bis dppe complex HFeCl dppe 2 is one of the most accessible transition metal hydrides Treatment of dppe with conventional oxidants such as hydrogen peroxide H2O2 aqueous bromine Br2 etc produces dppeO in low yield e g 13 as a result of non selective oxidation 4 Selective mono oxidation of dppe can be achieved by reaction with PhCH2Br to give dppeO Ph2P CH2 2PPh2 PhCH2Br Ph2P CH2 2PPh2 CH2Ph Br 2 3 Ph2P CH2 2PPh2 CH2Ph Br NaOH H2O Ph2P CH2 2P O Ph2 2 4 Hydrogenation of dppe gives the ligand bis dicyclohexylphosphino ethane Coordination complexes editMany 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 5 The natural bite angle is 86 6 Related compounds edit1 2 Bis dimethylphosphino ethane Bis diphenylphosphino methaneReferences edit W Hewertson and H R Watson 1962 283 The preparation of di and tri tertiary phosphines J Chem Soc 1490 1494 doi 10 1039 JR9620001490 Girolami G Rauchfuss T Angelici R Synthesis and Technique in Inorganic Chemistry 3rd ed University Science Books Sausalito CA 1999 pp 85 92 ISBN 0 935702 48 2 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 doi 10 1021 jo9907336 PMID 10814038 Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley amp Sons Ltd Cotton F A Wilkinson G Advanced Inorganic Chemistry A Comprehensive Text 4th ed Wiley Interscience Publications New York NY 1980 p 246 ISBN 0 471 02775 8 Birkholz nee Gensow Mandy Nicole Freixa Zoraida van Leeuwen Piet W N M 2009 Bite angle effects of diphosphines in C C and C X bond forming cross coupling reactions Chemical Society Reviews 38 4 1099 1118 doi 10 1039 B806211K PMID 19421583 Retrieved from https en wikipedia org w index php title 1 2 Bis diphenylphosphino ethane amp oldid 1157932876, wikipedia, wiki, book, books, library,
