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Fulvalene

1,1′-Bi[cyclopentadienylidene] Pentafulvalene Bicyclopentadienylidene [5,5′]Bicyclopentadienylidene

Fulvalene (bicyclopentadienylidene) is the member of the fulvalene family with the molecular formula C10H8. It is of theoretical interest as one of the simplest non-benzenoid conjugated hydrocarbons. Fulvalene is an unstable isomer of the more common benzenoid aromatic compounds naphthalene and azulene. Fulvalene consists of two 5-membered rings, each with two double bonds, joined by yet a fifth double bond. It has D2h symmetry.

History

An earlier attempt at synthesis of fulvalene in 1951 by Pauson and Kealy resulted in the accidental discovery of ferrocene.{{cite journal

Derivatives

Perchlorofulvalene (C4Cl4C)2 is quite stable in contrast to fulvalene itself.

References

References

  1. ''Dissertation Abstracts Int'l'' 26-06 page 3270 6411876.
  2. (1959). "Photochemical Experiments in Rigid Media at Low Temperatures. II. The Reactions of Methylene, Cyclopentadienylene and Diphenylmethylene". Journal of the American Chemical Society.
  3. (1986). "Synthese von Pentafulvalen durch oxidative Kupplung von Cyclopentadienid mittels Kupfer(II)-chlorid". Helvetica Chimica Acta.
  4. Mark, V.. (1966). "Perchlorofulvalene". Organic Syntheses.
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