Biferrocene
| Names | |
|---|---|
| IUPAC name
1,1"-Biferrocene
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| 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 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 into two fulvalene ligands.
Reactions
[edit | edit source]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
[edit | edit source]Aminophosphine ligands with biferroceno substituents have been prepared as catalysts for asymmetric allylic substitution[3] and asymmetric hydrogenation of alkenes.[4]
Related compounds
[edit | edit source]References
[edit | edit source]- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).