Biferrocene
Organometallic compound
From Wikipedia, the free encyclopedia
Biferrocene is the organometallic compound with the formula [(C5H5)Fe(C5H4)]2. It is the product of the formal dehydrocoupling of ferrocene, analogous the relationship between biphenyl and benzene. It is an orange, air-stable solid that is soluble in nonpolar organic solvents.
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| Names | |
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| IUPAC name
1,1"-Biferrocene | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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| Properties | |
| C20H18Fe2 | |
| Molar mass | 370.054 g·mol−1 |
| Appearance | dark orange solid |
| Melting point | 239–240 °C (462–464 °F; 512–513 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biferrocene can be prepared by the Ullmann coupling of iodoferrocene.[1] Its one-electron oxidized derivative [(C5H5)Fe(C5H4)]2+ attracted attention as a prototypical mixed-valence compound.[2]
A related compound is biferrocenylene, [Fe(C5H4)2]2 wherein all cyclopentadienyl rings are coupled into two fulvalene ligands.
Reactions
Biferrocene can easily be converted into a mixed-valence complex, which is called biferrocenium. This [Fe(II)-Fe(III)] cation is a class II type (0.707 > α > 0) mixed-valence complex according to the Robin-Day classification.[2]
Derivatives
Aminophosphine ligands with biferroceno substituents have been prepared as catalysts for asymmetric allylic substitution[3] and asymmetric hydrogenation of alkenes.[4]