Fulvene

Fulvene is one of several hydrocarbons with the same formula as benzene, C₆H₆. Fulvenes include the derivatives of this simple hydrocarbon, which itself is rarely encountered.^[1] Thiele is credited with discovering the scope of the reaction between cyclopentadiene and aldehydes and ketones that affords the brightly coloured fulvene derivatives.^[2] Most fulvenes are prepared by the reactions starting from cyclopentadiene or sodium cyclopentadienyl.^[3]

Structure of fulvene.

2,3,4,5-Tetramethylfulvene, abbreviated Me₄Fv, is a relatively common ligand in organometallic chemistry. It typically results from the deprotonation of cationic pentamethylcyclopentadienyl complexes.^[4]

References

1. ^ Bergmann, E. D. (1968). "Fulvenes and Substituted Fulvenes". Chemical Reviews 68: 41-84. doi:10.1021/cr60251a002.
2. ^ Thiele, J. (1900). "Ueber Ketonreactionen bei dem Cyclopentadiën". Chemische Berichte 33: 666-673. doi:/10.1002/cber.190003301113.
3. ^ Hafner, K.; Vöpel, K. H.; Ploss, G.; König, C. (1973). "6-(Dimethylamino)fulvene". Organic Syntheses Coll. Vol. 5: 431.
4. ^ Kreindlin, A. Z.; Rybinskaya, M. A. (2004). "Cationic and Neutral Transition Metal Complexes with a Tetramethylfulvene or Trimethylallyldiene Ligand". Russian Chemical Reviews 73: 417-432. doi:10.1070/RC2004v073n05ABEH000842.