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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.

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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.