Fulvalene
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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 aromatics naphthalene and azulene. It is also known as
bicyclopentadienylidene.
Fulvalene consists of two 5-membered rings, each with two double bonds, joined by yet a fifth double bond. It has D2h symmetry. It was long sought until 1958 when it was synthesized at Yale University by Edwin A. Matzner, working under William von Doering.[1]
Perchlorofulvalene C10Cl8 is quite stable in contrast to the hydrocarbon.[2]. Tetrathiafulvalene is an organic semiconductor.
[edit] Fulvalene as a ligand in organometallic chemistry
Fulvalene forms stable organometallic complexes, which can be formally considered derivatives of the dianion C10H82-. [3] Some such fulvalene complexes undergo reversible C-C bond scission.[4]
[edit] References
- ^ Dissertation Abstracts Int'l 26-06 page 3270 6411876.
- ^ Mark, V. “Perchlorofulvalene” Organic Syntheses, Collected Volume 5, p.901 (1973).
- ^ 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.
