1,1'-Bis(diphenylphosphino)ferrocene

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1,1'-Bis(diphenylphosphino)ferrocene


IUPAC name 1,1'- bis( diphenylphosphanyl) ferrocene
Other names 1,1'- Bis( diphenylphosphino) ferrocene, 1,1'- Ferrocenediyl- bis(diphenylphosphine), Dppf, 1,1'- Ferrocenebis (diphenylphosphine)
Identifiers
CAS number	12150-46-8
PubChem	635956
ChemSpider	21865114^Y
ChEBI	CHEBI:30743
Jmol-3D images	Image 1 Image 2
SMILES 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] c1ccc(cc1)P(c2ccccc2)C34C5[Fe]3678912(C5C6C74)C3C8C9C1(C23)P(c1ccccc1)c1ccccc1
InChI InChI=1S/2C17H14P.Fe/c21-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h21-14H;^Y Key: HPXNTHKXCYMIJL-UHFFFAOYSA-N^Y InChI=1/2C17H14P.Fe/c21-3-9-15(10-4-1)18(17- -13-7-8-14-17)16-11-5-2-6-12-16;/h21-14H;/q2-1;+2 Key: HPXNTHKXCYMIJL-UHFFFAOYSA-N InChI=1/2C17H14P.Fe/c21-3-9-15(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 Key: HPXNTHKXCYMIJL-KDKHWAOJAX
Properties
Molecular formula	C₃₄H₂₈FeP₂
Molar mass	554.391
Melting point	181-183 °C
Hazards
R-phrases	R25
S-phrases	S28A S45
Main hazards	Toxic
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,1'-Bis(diphenylphosphino)ferrocene, commonly abbreviated dppf, is an organophosphorous compound commonly used as a ligand in homogeneous catalysis. It contains a ferrocene moiety in its backbone, and is related to other bridged diphosphines 1,2-bis(diphenylphosphino)ethane (dppe).

Contents

1 Preparation
2 Reactions
3 See also
4 References

Preparation

This 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.

Reactions

Dppf 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)

Structure of the complex PtCl₂(dppf).

References

^ Ian R. Butler (2010). "3.15 The Use of Organolithium Reagents in the Preparation of Ferrocene Derivatives". In J. Derek Woollins (Google Books excerpt). Inorganic Experiments. pp. 175–179. ISBN 978-3-527-32472-9. http://books.google.com/books?id=IlL_qLqj_nUC&pg=PA173.
^ ^a ^b Nataro, Chip; Fosbenner, Stephanie M. (2009). "Synthesis and Characterization of Transition-Metal Complexes Containing 1,1'-Bis(diphenylphosphino)ferrocene". J. Chem. Ed. 86 (12): 1412. doi:10.1021/ed086p1412.

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