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1,2-Bis(diphenylphosphino)ethane

Diphos Dppe

1,2-Bis(diphenylphosphino)ethane (dppe) is an organophosphorus compound with the formula (PhPCH) (Ph = phenyl). It is a common symmetrical bidentate ligand in coordination chemistry. It is a white solid that is soluble in organic solvents.

Preparation

The preparation of dppe entails the alkylation of NaP(C6H5)2 with 1,2-dichloroethane: :

Reactions

The reduction of dppe by lithium give the disecondary phosphine:{{cite journal : Hydrolysis gives the bis(secondary phosphine). : :[[Image:HFeCl dppe 2.svg|thumb|left|The bis(dppe) complex [[Chlorobis(dppe)iron hydride|HFeCl(dppe)]] is one of the most accessible transition metal hydrides.]]

Treatment of dppe with hydrogen peroxide produces the phosphine oxides . Selective mono-oxidation of dppe can be achieved by benzylation followed by hydrolysis: : :

Hydrogenation of dppe gives the ligand bis(dicyclohexylphosphino)ethane.

Coordination complexes

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)(dppe)) and of bridging behavior. The natural bite angle is 86°.

References

References

  1. W. Hewertson and H. R. Watson. (1962). "283. The preparation of di- and tri-tertiary phosphines". [[J. Chem. Soc.]].
  2. 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
  3. Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley & Sons, Ltd
  4. 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
  5. (2009). "Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions". Chemical Society Reviews.
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chelating-agents diphosphines phenyl-compounds 1,2-ethanediyl-compounds
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