Biferrocene

Biferrocene
Identifiers
CAS Number	1287-38-3;
3D model (JSmol)	Interactive image;
ChemSpider	10157133;
PubChem CID	11984633;
	InChI InChI=1S/C10H8.2C5H5.2Fe/c1-2-6-9(5-1)10-7-3-4-8-10;21-2-4-5-3-1;;/h1-8H;21-5H;;/q-6;2*-1;; Key: CEMHVYUXQJEPPO-UHFFFAOYSA-N;
	SMILES [c1cccc1]-[Fe]-[c2cccc23].[c13cccc1]-[Fe]-[c2cccc2];
Properties
Chemical formula	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).
	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[]

^ M. D. Rausch (1961). "Ferrocene and Related Organometallic π-Complexes. IV. Some Ullmann Reactions of Haloferrocenes". J. Org. Chem. 26 (6): 1802–1805. doi:10.1021/jo01065a026.
^ Cowan, D. O.; LeVanda, C.; Park, J.; Kaufman, F. (1973). "Organic Solid State. VIII. Mixed-Valence Ferrocene Chemistry". Acc. Chem. Res. 6: 1–7. doi:10.1021/ar50061a001.CS1 maint: uses authors parameter (link)

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[1] M. D. Rausch (1961). "Ferrocene and Related Organometallic π-Complexes. IV. Some Ullmann Reactions of Haloferrocenes". J. Org. Chem. 26 (6): 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". Acc. Chem. Res. 6: 1–7. doi:10.1021/ar50061a001.CS1 maint: uses authors parameter (link)

[1]

[2]

Identifiers

CAS Number	1287-38-3
3D model (JSmol)	Interactive image
ChemSpider	10157133
PubChem CID	11984633
InChI InChI=1S/C10H8.2C5H5.2Fe/c1-2-6-9(5-1)10-7-3-4-8-10;21-2-4-5-3-1;;/h1-8H;21-5H;;/q-6;2*-1;; Key: CEMHVYUXQJEPPO-UHFFFAOYSA-N
SMILES [c1cccc1]-[Fe]-[c2cccc23].[c13cccc1]-[Fe]-[c2cccc2]
Properties
Chemical formula	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).
Infobox references