Bis(fulvalene)diiron

Bis(fulvalene)diiron
Names
	Other names Biferrocenylene
Identifiers
CAS Number	11105-90-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	10157150;
PubChem CID	11984650;
	InChI InChI=1S/2C10H8.2Fe/c21-2-6-9(5-1)10-7-3-4-8-10;;/h21-8H;;/q-6;-2;; Key: RQVWSKGUQRKYKR-UHFFFAOYSA-N;
	SMILES [CH-]1[CH-][CH-][C-]([CH-]1)[C-]2C=CC=C2.C1=C[C-](C=C1)[C-]2C=CC=C2.[Fe].[Fe];
Properties
Chemical formula	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

Related compounds

Biferrocene

References

Churchill, Melvyn R.; Wormald, John (1969). "Crystal and molecular structure of bis(fulvalene)diiron". Inorganic Chemistry. 8 (9): 1970–1974. doi:10.1021/ic50079a030.
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.
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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[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.