Biferrocene

Biferrocene
Identifiers
Properties
C20H18Fe2
Molar mass 370.05 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).
Infobox references

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.

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. Formally, biferrocene is derived from one fulvalene ligand, and biferrocenylene is derived from two.

References

  1. ↑ M. D. Rausch (1961). "Ferrocene and Related Organometallic π-Complexes. IV. Some Ullmann Reactions of Haloferrocenes". J. Org. Chem. 26: 1802–1805. doi:10.1021/jo01065a026.
  2. ↑ Cowan, D. O.; LeVanda, C.; Park, J.; Kaufman, F. (1973). "Organic Solid State. VIII. Mixed-Valence Ferrocene Chemistry". Accounts Chem. Res. 6: 1–7. doi:10.1021/ar50061a001.
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