1,2-Bis(diphenylphosphino)ethane (dppe) is an

organophosphorus compound Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbo ...

with the formula (PhPCH) (Ph =

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...

). It is a common symmetrical bidentate ligand in

coordination chemistry A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...

. It is a white solid that is soluble in organic solvents.

Preparation

The preparation of dppe entails the

alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

of NaP(C₆H₅)₂ with 1,2-dichloroethane: :

Reactions

The reduction of dppe by

lithium Lithium (from , , ) is a chemical element; it has chemical symbol, symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard temperature and pressure, standard conditions, it is the least dense metal and the ...

give the disecondary phosphine: : Hydrolysis gives the bis(secondary phosphine). : : Treatment of dppe with

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...

produces the

phosphine oxide Phosphine oxide is the inorganic compound with the formula H3PO. Although stable as a dilute gas, liquid or solid samples are unstable. Unlike many other compounds of the type POxHy, H3PO is rarely discussed and is not even mentioned in major so ...

s .Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley & Sons, Ltd Selective mono-oxidation of dppe can be achieved by benzylation followed by hydrolysis: : : Hydrogenation of dppe gives the ligand

bis(dicyclohexylphosphino)ethane Bis(dicyclohexylphosphino)ethane, abbreviated dcpe, is an organophosphorus compound with the formula (C6H11)2PCH2CH2P(C6H11)2. It is a white solid that is soluble in nonpolar organic solvents. The compound is used as a bulky and highly basic dip ...

Coordination complexes

Many coordination complexes of dppe are known, and some are used as homogeneous catalysts. Dppe is almost invariably

chelating Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...

, although there are examples of monodentate (e.g., W(CO)(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. The natural

bite angle In coordination chemistry, the bite angle is the angle on a central atom between two bonds to a bidentate ligand. This ligand–metal–ligand geometric parameter is used to classify chelation, chelating ligands, including those in organometallic ...

is 86°.

Related compounds

1,2-Bis(dimethylphosphino)ethane 1,2-Bis(dimethylphosphino)ethane (dmpe) is a diphosphine ligand in coordination chemistry. It is a colorless, air-sensitive liquid that is soluble in organic solvents. With the formula (CHPMe), dmpe is used as a compact strongly basic spectator ...

* Bis(diphenylphosphino)methane

References

{{DEFAULTSORT:Bisdiphenylphosphinoethane Chelating agents Diphosphines Phenyl compounds 1,2-Ethanediyl compounds