Bis(fulvalene)diiron

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Bis(fulvalene)diiron
Fv2Fe2.svg
Names
Other names
Biferrocenylene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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
  • C1=C[C-](C=C1)[C-]2C=CC=C2.[Fe+2].[Fe+2].C1=C[C-](C=C1)[C-]2C=CC=C2
Properties
C20H16Fe2
Molar mass 368.038 g·mol−1
Appearanceorange 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).

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]

Contents

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

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5
H
5
, abbreviated Cp) bound to a metal center (M) in the oxidation state II, with the resulting general formula (C5H5)2M. Closely related to the metallocenes are the metallocene derivatives, e.g. titanocene dichloride or vanadocene dichloride. Certain metallocenes and their derivatives exhibit catalytic properties, although metallocenes are rarely used industrially. Cationic group 4 metallocene derivatives related to [Cp2ZrCH3]+ catalyze olefin polymerization.

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3
COCHCOCH
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5
H
7
O
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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.