Biferrocene

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Biferrocene
Names
IUPAC name
1,1"-Biferrocene
Identifiers
3D model (
JSmol
)
ChemSpider
  • InChI=1S/C10H8.2C5H5.2Fe/c1-2-6-9(5-1)10-7-3-4-8-10;2*1-2-4-5-3-1;;/h1-8H;2*1-5H;;/q-6;2*-1;;
    Key: CEMHVYUXQJEPPO-UHFFFAOYSA-N
  • C1=C[CH-]C=C1.[Fe+2].C2=C[C-](C=C2)[C-](C=C3)C=C3.[Fe+2].C1=C[CH-]C=C1
Properties
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).

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

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.

Reactions

Biferrocene can easily be converted into a mixed-valence complex, which is called biferrocenium. This [Fe(II)-Fe(III)] cation is a class II type (0.707 > α > 0) mixed-valence complex according to the Robin-Day classification.[2]

Derivatives

Aminophosphine ligands with biferroceno substituents have been prepared as catalysts for asymmetric allylic substitution[3] and asymmetric hydrogenation of alkenes.[4]

Related compounds

References

  1. doi:10.1021/jo01065a026
    .
  2. ^
    doi:10.1021/ar50061a001
    .
  3. PMID 11925230
    .
  4. PMID 24795493
    .
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