My watch list

Fulvalene

Fulvalene is an organic compound 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 compoundss naphthalene and azulene. It is also known as bicyclopentadienylidene.

Additional recommended knowledge

What is the Correct Way to Check Repeatability in Balances?

Daily Sensitivity Test

Recognize and detect the effects of electrostatic charges on your balance

Fulvalene consists of two 5-membered rings, each with two double bonds, joined by yet a fifth double bond. It has D_2h symmetry. It was long sought until 1958 when it was synthesized at Yale University by E. A. Matzner, working under W. von Doering.^[1]

Perchlorofulvalene C₁₀Cl₈ is quite stable in contrast to the hydrocarbon.^[2]. Tetrathiafulvalene is an organic semiconductor.

Fulvalene as a ligand in organometallic chemistry

Fulvalene forms stable organometallic complexes that can be formally considered derivatives of the dianion C₁₀H₈^2-. ^[3] Some such fulvalene complexes undergo reversible C-C bond scission.^[4]

References

^ Dissertation Abstracts Int'l 26-06 page 3270 6411876.
^ Mark, V. “Perchlorofulvalene” Organic Syntheses, Collected Volume 5, p.901 (1973).http://www.orgsyn.org/orgsyn/pdfs/CV5P0901.pdf
^ Capps, K. B.; Whitener, G. D.; Bauer, A.; Abboud, K. A.; Wasser, I. M.; Vollhardt, K. P. C. and Hoff, C. D., "Synthesis and Crystal Structures of (Fulvalene)W₂(SH)₂(CO)₆, (Fulvalene)W₂(μ-S₂)(CO)₆, and (Fulvalene)W₂(μ-S)(CO)₆: Low Valent Tungsten Carbonyl Sulfide and Disulfide Complexes Stabilized by the Bridging Fulvalene Ligand", Inorganic Chemistry, 2002, volume 41, pages 3212 -3217.
^ Boese, R. J.; Cammack, K.; Matzger, A. J.; Pflug, K.; Tolman,W. B.; Vollhardt, K. P. C.; Weidman, T. W. "Photochemistry of (Fulvalene)tetracarbonyldiruthenium and Its Derivatives: Efficient Light Energy Storage Devices" Journal of the American Chemistry Society 1997, volume 119, p. 6757-6773.