1,2-Bis(diphenylphosphino)benzene

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1,2-Bis(diphenylphosphino)benzene
Dppbz.svg
Names
Other names
o-Phenylenebis[diphenylphosphine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C30H24P2/c1-5-15-25(16-6-1)31(26-17-7-2-8-18-26)29-23-13-14-24-30(29)32(27-19-9-3-10-20-27)28-21-11-4-12-22-28/h1-24H
    Key: NFRYVRNCDXULEX-UHFFFAOYSA-N
  • C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3P(C4=CC=CC=C4)C5=CC=CC=C5
Properties
C30H24P2
Molar mass 446.470 g·mol−1
Appearancewhite solid
Melting point 185–187 °C (365–369 °F; 458–460 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,2-Bis(diphenylphosphino)benzene (dppbz) is an organophosphorus compound with the formula C6H4(PPh2)2 (Ph = C6H5). Classified as a diphosphine ligand, it is a common bidentate ligand in coordination chemistry. [1] It is a white, air-stable solid. [2] As a chelating ligand, dppbz is very similar to 1,2-bis(diphenylphosphino)ethylene.

Related Research Articles

Ferrocene is an organometallic compound with the formula Fe(C5H5)2. The molecule is a complex consisting of two cyclopentadienyl rings bound to a central iron atom. It is an orange solid with a camphor-like odor, that sublimes above room temperature, and is soluble in most organic solvents. It is remarkable for its stability: it is unaffected by air, water, strong bases, and can be heated to 400 °C without decomposition. In oxidizing conditions it can reversibly react with strong acids to form the ferrocenium cation Fe(C5H5)+2.

BINAP Chemical compound

BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) is an organophosphorus compound. This chiral diphosphine ligand is widely used in asymmetric synthesis. It consists of a pair of 2-diphenylphosphinonaphthyl groups linked at the 1 and 1′ positions. This C2-symmetric framework lacks a stereogenic atom, but has axial chirality due to restricted rotation (atropisomerism). The barrier to racemization is high due to steric hindrance, which limits rotation about the bond linking the naphthyl rings. The dihedral angle between the naphthyl groups is approximately 90°. The natural bite angle is 93°.

1,2-Bis(diphenylphosphino)ethane Chemical compound

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.

Hapticity

Hapticity is the coordination of a ligand to a metal center via an uninterrupted and contiguous series of atoms. The hapticity of a ligand is described with the Greek letter η ('eta'). For example, η2 describes a ligand that coordinates through 2 contiguous atoms. In general the η-notation only applies when multiple atoms are coordinated. In addition, if the ligand coordinates through multiple atoms that are not contiguous then this is considered denticity, and the κ-notation is used once again. When naming complexes care should be taken not to confuse η with μ ('mu'), which relates to bridging ligands.

Sandwich compound Type of chemical compound

In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by haptic covalent bonds to two arene ligands. The arenes have the formula CnHn, substituted derivatives (for example Cn(CH3)n) and heterocyclic derivatives (for example BCnHn+1). Because the metal is usually situated between the two rings, it is said to be "sandwiched". A special class of sandwich complexes are the metallocenes.

Bis(benzene)chromium Chemical compound

Bis(benzene)chromium is the organometallic compound with the formula Cr(η6-C6H6)2. It is sometimes called dibenzenechromium. The compound played an important role in the development of sandwich compounds in organometallic chemistry and is the prototypical complex containing two arene ligands.

1,1-Bis(diphenylphosphino)ferrocene Chemical compound

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).

1,2-Bis(dimethylarsino)benzene Chemical compound

1,2-Bis(dimethylarsino)benzene (diars) is the organoarsenic compound with the formula C6H4(As(CH3)2)2. The molecule consists of two dimethylarsino groups attached to adjacent carbon centers of a benzene ring. It is a chelating ligand in coordination chemistry. This colourless oil is commonly abbreviated "diars."

Diphenylphosphine Chemical compound

Diphenylphosphine, also known as diphenylphosphane, is an organophosphorus compound with the formula (C6H5)2PH. This foul-smelling, colorless liquid is easily oxidized in air. It is a precursor to organophosphorus ligands for use as catalysts.

Bis(diphenylphosphino)methane Chemical compound

1,1-Bis(diphenylphosphino)methane (dppm), is an organophosphorus compound with the formula CH2(PPh2)2. Dppm, a white, crystalline powder, is used in inorganic and organometallic chemistry as a ligand. It is more specifically a chelating ligand because it is a ligand that can bond to metals with two phosphorus donor atoms. The natural bite angle is 73°.

Chemical vapor deposition of ruthenium is a method to deposit thin layers of ruthenium on substrates by Chemical vapor deposition (CVD).

(1,1-Bis(diphenylphosphino)ferrocene)palladium(II) dichloride Chemical compound

[1,1'‑Bis(diphenylphosphino)ferrocene]palladium(II) dichloride is a palladium complex containing the bidentate ligand 1,1'-bis(diphenylphosphino)ferrocene (dppf), abbreviated as [(dppf)PdCl2]. This commercially available material can be prepared by reacting dppf with a suitable nitrile complex of palladium dichloride:

Metal-phosphine complex

A metal-phosphine complex is a In coordination complex containing one or more phosphine ligands. Almost always, the phosphine is an organophosphine of the type R3P (R = alkyl, aryl). Metal phosphine complexes are useful in homogeneous catalysis. Prominent examples of metal phosphine complexes include Wilkinson's catalyst (Rh(PPh3)3Cl), Grubbs' catalyst, and tetrakis(triphenylphosphine)palladium(0).

Half sandwich compound

Half sandwich compounds are organometallic complexes that feature a cyclic polyhapto ligand bound to an MLn center, where L is a unidentate ligand. Thousands of such complexes are known. Well-known examples include cyclobutadieneiron tricarbonyl and (C5H5)TiCl3. Commercially useful examples include (C5H5)Co(CO)2, which is used in the synthesis of substituted pyridines, and methylcyclopentadienyl manganese tricarbonyl, an antiknock agent in petrol.

DIOP Chemical compound

DIOP is an organophosphorus compound that is used as a chiral ligand in asymmetric catalysis. It is a white solid that is soluble in organic solvents.

Chlorobis(dppe)iron hydride Chemical compound

Chlorobis(dppe)iron hydride is a coordination complex with the formula HFeCl(dppe)2, where dppe is the bidentate ligand 1,2-bis(diphenylphosphino)ethane. It is a red-violet solid. The compound has attracted much attention as a precursor to dihydrogen complexes.

In organic chemistry, peri-naphthalenes are particular derivatives of naphthalene with the formula C10H6-1,8-X2. Owing to the rigidity of the naphthalene skeleton, these substituents on the 1- and 8-positions are constrained to be relatively close 2.5 Å, which is within the van der Waals radius for many atoms. In contrast, ortho-substituents pendant from a benzene ring are separated by about 3.3 Å.

1,4-Bis(diphenylphosphino)butane Chemical compound

1,4-Bis(diphenylphosphino)butane (dppb) is an organophosphorus compound with the formula (Ph2PCH2CH2)2. It is less commonly used in coordination chemistry than other diphosphine ligands such as dppe. It is a white solid that is soluble in organic solvents.

1,2-Bis(dichlorophosphino)benzene Chemical compound

1,2-Bis(dichlorophosphino)benzene is an organophosphorus compound with the formula C6H4(PCl2)2. A viscous colorless liquid, it is a precursor to chelating diphosphines of the type C6H4(PR2)2. It is prepared from 1,2-dibromobenzene by sequential lithiation followed by treatment with (Et2N)2PCl (Et = ethyl), which affords C6H4[P(NEt2)2]2. This species is finally cleaved with hydrogen chloride:

cis-1,2-Bis(diphenylphosphino)ethylene (dppv) is an organophosphorus compound with the formula C2H2(PPh2)2 (Ph = C6H5). Both the cis and trans isomers are known, but the cis isomer is of primary interest. Classified as a diphosphine ligand, it is a bidentate ligand in coordination chemistry. For example it gives rise to the complex Ni(dppv)2 and the coordination polymer [Ni(dppv)]n. As a chelating ligand, dppv is very similar to 1,2-bis(diphenylphosphino)benzene.

References

  1. Hatakeyama, Takuji; Kondo, Yoshiyuki; Fujiwara, Yu-Ichi; Takaya, Hikaru; Ito, Shingo; Nakamura, Eiichi; Nakamura, Masaharu (2009). "Iron-catalysed fluoroaromatic coupling reactions under catalytic modulation with 1,2-bis(diphenylphosphino)benzene". Chemical Communications (10): 1216–1218. doi:10.1039/B820879D. PMID   19240878.
  2. Csákÿ, Aurelio G.; Molina, María Teresa (2011). "1,2-Bis(diphenylphosphino)benzene". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01300. ISBN   978-0471936237.