Bis(fulvalene)diiron
Names
Other names
Biferrocenylene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/2C10H8.2Fe/c2*1-2-6-9(5-1)10-7-3-4-8-10;;/h2*1-8H;;/q-6;-2;;
    Key: RQVWSKGUQRKYKR-UHFFFAOYSA-N
  • [CH-]1[CH-][CH-][C-]([CH-]1)[C-]2C=CC=C2.C1=C[C-](C=C1)[C-]2C=CC=C2.[Fe].[Fe]
Properties
C20H16Fe2
Molar mass 368.038 g·mol−1
Appearance orange solid
Density 1.76 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bis(fulvalene)diiron is the organoiron complex with the formula (C5H4-C5H4)2Fe2. Structurally, the molecule consists of two ferrous centers sandwiched between fulvalene dianions. The compound is an orange solid with lower solubility in benzene than ferrocene. Its structure has been verified by X-ray crystallography.[1] The compound has attracted some interest for its redox properties.[2]

Preparation

It was first prepared by Ullmann coupling of 1,1'-diiodoferrocene using copper but subsequent work produces the complex is 20-40% yield from dilithiofulvalene and ferrous chloride:[3]

2 (C5H4Li)2 + 2 FeCl2 → (C5H4-C5H4)2Fe2 + 4 LiCl

References

  1. ↑ Churchill, Melvyn R.; Wormald, John (1969). "Crystal and molecular structure of bis(fulvalene)diiron". Inorganic Chemistry. 8 (9): 1970–1974. doi:10.1021/ic50079a030.
  2. ↑ Brüggeller, Peter; Jaitner, Peter; Schottenberger, Herwig (1991). "Kristallographische Gegenüberstellung der Monokationen von Bis(fulvalen)dieisien und Bis(fulvalen) Eisen-Cobalt mit Identischem Gegenion (PF6−)". Journal of Organometallic Chemistry. 417 (3): C53–C58. doi:10.1016/0022-328X(91)80206-Y.
  3. ↑ Levanda, Carole; Bechgaard, Klaus; Cowan, Dwaine O.; Mueller-Westerhoff, Ulrich T.; Eilbracht, Peter; Candela, George A.; Collins, R. L. (1976). "Bis(fulvalene)diiron, Its Mono- and Dications. Intramolecular Exchange Interactions in a Rigid System". Journal of the American Chemical Society. 98 (11): 3181–3187. doi:10.1021/ja00427a021.
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