Fulvalene

Fulvalene

. 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 E. A. Matzner, working under William von Eggers Doering. ["Dissertation Abstracts Int'l" 26-06 page 3270 6411876.] An earlier attempt in 1951 by Pauson and Kealy resulted in the accidental discovery of ferrocene. [cite journal
author = T. J. Kealy, P. L. Pauson
title = A New Type of Organo-Iron Compound
journal = Nature
year = 1951
volume = 168
pages = 1039
doi = 10.1038/1681039b0]

Perchlorofulvalene C10Cl8 is quite stable in contrast to the hydrocarbon. [Mark, V. “Perchlorofulvalene” Organic Syntheses, Collected Volume 5, p.901 (1973).http://www.orgsyn.org/orgsyn/pdfs/CV5P0901.pdf] . 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 C10H82−. [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.] Some such fulvalene complexes undergo reversible C-C bond scission. [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.]

References


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