Biferrocene

Today we want to talk about Biferrocene, a topic that has gained great relevance in recent times. Biferrocene is a topic that generates conflicting opinions and that has been the subject of debate in different areas. Its importance lies in the impact it has on today's society and how it influences people's daily lives. In this article we will explore different aspects related to Biferrocene, analyzing its implications and its relevance today. Without a doubt, Biferrocene is a topic that does not leave anyone indifferent and that deserves to be thoroughly understood.

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=CC=C1..C2=C(C=C2)(C=C3)C=C3..C1=CC=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 , 100 kPa).

Biferrocene is the organometallic compound with the formula 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 2+ attracted attention as a prototypical mixed-valence compound.[2]

A related compound is biferrocenylene, 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 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]

References

  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. ^ a b 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.
  3. ^ Xiao, Li; Weissensteiner, Walter; Mereiter, Kurt; Widhalm, Michael (2002-03-08). "Novel Chiral Biferrocene Ligands for Palladium-Catalyzed Allylic Substitution Reactions". The Journal of Organic Chemistry. 67 (7): 2206–2214. doi:10.1021/jo016249w. ISSN 0022-3263. PMID 11925230.
  4. ^ Zirakzadeh, Afrooz; Groß, Manuela A.; Wang, Yaping; Mereiter, Kurt; Weissensteiner, Walter (2014-04-09). "Walphos versus Biferrocene-Based Walphos Analogues in the Asymmetric Hydrogenation of Alkenes and Ketones". Organometallics. 33 (8): 1945–1952. doi:10.1021/om401074a. ISSN 0276-7333. PMC 4006446. PMID 24795493.