Biferrocene is the

organometallic compound Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and so ...

with the formula C₅H₅)Fe(C₅H₄)sub>2. It is the product of the formal dehydrocoupling of

ferrocene Ferrocene is an organometallic compound with the formula . 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, a ...

, analogous the relationship between biphenyl and benzene. It is an orange, air-stable solid that is soluble in nonpolar organic solvents. Biferrocene can be prepared by the Ullmann coupling of iodoferrocene. Its one-electron oxidized derivative C₅H₅)Fe(C₅H₄)sub>2⁺ attracted attention as a prototypical mixed-valence compound. A related compound is biferrocenylene, e(C₅H₄)₂sub>2 wherein all

cyclopentadienyl Cyclopentadienyl can refer to *Cyclopentadienyl anion, or cyclopentadienide, **Cyclopentadienyl ligand *Cyclopentadienyl radical, • *Cyclopentadienyl cation, See also *Pentadienyl In organic chemistry, pentadienyl refers to the organic radic ...

rings are coupled. Formally, biferrocene is derived from one

fulvalene Fulvalene (bicyclopentadienylidene) is the member of the fulvalene family with the molecular formula C10H8. It is of theoretical interest as one of the simplest non-benzenoid conjugated hydrocarbons. Fulvalene is an unstable isomer of the mor ...

ligand, and biferrocenylene is derived from two.

Reactions

Biferrocene can easily be converted into a

mixed-valence complex Mixed valence complexes contain an element which is present in more than one oxidation state. Well-known mixed valence compounds include the Creutz–Taube complex, Prussian blue, and molybdenum blue. Many solids are mixed-valency including in ...

, which is called biferrocenium. This e(II)-Fe(III)cation is a class II type (0.707 > α > 0) mixed-valence complex according to the Robin-Day classification.

Derivatives

Aminophosphine In organophosphorus chemistry, an aminophosphine is a compound with the formula R3−nP(NR2)n where R = H or an organic substituent, and n = 0, 1, 2. At one extreme, the parent H2PNH2 is lightly studied and fragile, but at the other extreme tris(di ...

ligands with biferroceno substitutents have been prepared as catalysts for asymmetric

allylic substitution An allylic rearrangement or allylic shift is an organic reaction in which the double bond in an allyl chemical compound shifts to the next carbon atom. It is encountered in nucleophilic substitution. In reaction conditions that favor a SN1 reactio ...

and

asymmetric hydrogenation Asymmetric hydrogenation is a chemical reaction that adds two atoms of Hydrogen atom, hydrogen to a target (substrate) molecule with three-dimensional Enantioselective synthesis, spatial selectivity. Critically, this selectivity does not come from ...

of alkenes.

Related compounds

* Bis(fulvalene)diiron

References

Ferrocenes Sandwich compounds Cyclopentadienyl complexes {{Inorganic-compound-stub