| 词条 | 1,1'-Bis(diphenylphosphino)ferrocene |
| 释义 |
| Verifiedfields = correct | Watchedfields = changed | verifiedrevid = 477199791 | ImageFile = Dppfnew.png | ImageSize = 150 px | ImageFile1 = Dppf-from-xtal-3D-balls.png | ImageSize1 = 250 px | IUPACName = 1,1'- bis( diphenylphosphanyl) ferrocene | OtherNames = 1,1'- Bis( diphenylphosphino) ferrocene, 1,1'- Ferrocenediyl- bis(diphenylphosphine), Dppf, 1,1'- Ferrocenebis (diphenylphosphine) |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 30743 | ChemSpiderID = 21865114 | InChI = 1/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17- -13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H;/q2*-1;+2 | InChIKey = HPXNTHKXCYMIJL-UHFFFAOYSA-N | InChI1 = 1/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H;/rC34H28FeP2/c1-5-13-21(14-6-1)36(22-15-7-2-8-16-22)33-29-25-26-30(33)35(25,26,29,33)27-28(35)32(35)34(35,31(27)35)37(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20,25-32H | InChIKey1 = HPXNTHKXCYMIJL-KDKHWAOJAX | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H; | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HPXNTHKXCYMIJL-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|chemspider}} | CASNo = 12150-46-8 | PubChem = 635956 | SMILES1 = c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1 | SMILES2 = C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2] |Section2={{Chembox Properties | Formula = C34H28FeP2 | MolarMass = 554.391 | Appearance = | Density = | MeltingPtC = 181 to 183 | MeltingPt_notes = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = Toxic | FlashPt = | AutoignitionPt = | RPhrases = {{R25}} | SPhrases = {{S28}}A {{S45}} }} 1,1'-Bis(diphenylphosphino)ferrocene, commonly abbreviated dppf, is an organophosphorus compound commonly used as a ligand in homogeneous catalysis. It contains a ferrocene moiety in its backbone, and is related to other bridged diphosphines such as 1,2-bis(diphenylphosphino)ethane (dppe). PreparationThis compound is commercially available. It may be prepared by treating dilithioferrocene with chlorodiphenylphosphine:[1] Fe(C5H4Li)2 + 2 ClPPh2 → Fe(C5H4PPh2)2 + 2 LiCl The dilithiation of ferrocene is easily achieved with n-butyllithium in the presence of TMEDA. Many related ligands can be made in this way. The Fe center is typically not involved in the behavior of the ligand. ReactionsDppf readily forms metal complexes.[2] The palladium derivative, (dppf)PdCl2, which is popular for palladium-catalyzed coupling reactions, is prepared by treating dppf with the acetonitrile or benzonitrile adducts of palladium dichloride:[2] dppf + PdCl2(RCN)2 → (dppf)PdCl2 + 2 RCN (RCN = acetonitrile or benzonitrile){{clear left}} See also
References1. ^{{cite book | chapter = 3.15 The Use of Organolithium Reagents in the Preparation of Ferrocene Derivatives | author = Ian R. Butler | editor = J. Derek Woollins | year = 2010 | isbn = 978-3-527-32472-9 | title = Inorganic Experiments | pages = 175–179 | url = https://books.google.com/books?id=IlL_qLqj_nUC&pg=PA173 | format = Google Books excerpt}} {{DEFAULTSORT:Bisdiphenylphosphinoferrocene, 1,1'-}}2. ^1 {{cite journal | last1 = Nataro | first1 = Chip | last2 = Fosbenner | first2 = Stephanie M. | title = Synthesis and Characterization of Transition-Metal Complexes Containing 1,1'-Bis(diphenylphosphino)ferrocene | journal = J. Chem. Educ. | volume = 86 | pages = 1412 | year = 2009 | doi = 10.1021/ed086p1412 | issue = 12}} 3 : Ferrocenes|Tertiary phosphines|Bisphosphanes |
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