A fulvalene is a hydrocarbon obtained by formally cross-conjugating two rings through a common exocyclic double bond.[1] The name is derived from the similarly structured fulvenes which lack one ring. Pentafulvalene (2) is also called simply fulvalene, the parent structure of this class. Triapentafulvalene (3) is also known as calicene from the words calix or chalice because of its wine-glass appearance.
In general, the parent fulvalenes are very unstable; for instance, the parent triafulvalene (1) has never been synthesized. On the other hand, stable fulvalenes can be obtained by proper substitution or benzannulation. Several members should be stabilized taking into account a dipolar mesomeric form with for instance sesquifulvalene 4, which can be thought of as a tropylium cation joined to a cyclopentadienyl anion (both stable and aromatic). In this compound the dipolar structure is calculated to contribute 23% to the total structure.
^The Fulvalenes, Brian Halton, Eur. J. Org. Chem. 2005, 3391–3414 doi:10.1002/ejoc.200500231
parent fulvalenes are very unstable; for instance, the parent triafulvalene (1) has never been synthesized. On the other hand, stable fulvalenes can be...
Fulvalene (bicyclopentadienylidene) is the member of the fulvalene family with the molecular formula C10H8. It is of theoretical interest as one of the...
Pauson and Thomas J. Kealy at Duquesne University attempted to prepare fulvalene ((C5H4)2) by oxidative dimerization of cyclopentadiene (C5H6). To that...
(1986), "Synthetic and NMR spectroscopic investigations of fulvenes and fulvalenes" (PDF), Pure Appl. Chem., 58 (1): 55–66, doi:10.1351/pac198658010055,...
exact mass: 128.0626 u) may refer to: Azulene Bicyclo[6.2.0]decapentaene Fulvalene Naphthalene This set index page lists chemical structure articles associated...
(1986), "Synthetic and NMR spectroscopic investigations of fulvenes and fulvalenes" (PDF), Pure Appl. Chem., 58 (1): 55–66, doi:10.1351/pac198658010055 IUPAC...
π-Electronic Structure of Singlet, Triplet, and Quintet States of Fulvenes and Fulvalenes Using the Electron Localization Function". The Journal of Physical Chemistry...
development of molecular electronics. TTF is related to the hydrocarbon fulvalene, (C5H4)2, by replacement of four CH groups with sulfur atoms. Over 10...
Telluride based batteries convert 15 to 20 percent of heat to energy. Fulvalene diruthenium promises greater efficiency, but is too expensive for commercial...
allene: Attempted synthesis of "titanocene", i.e. Ti(C5H5)2, produces a fulvalene complex. The titanocene dimer was recognised in the 1970s but not structurally...
titanocene by reduction of titanocene dichloride affords complexes of fulvalene ligands. Bent metallocenes derived from pentamethylcyclopentadiene can...
at 237 to 254 nm forms small amounts of fulvene along with benzvalene. Fulvalene Methylenecyclopropene Nomenclature of Organic Chemistry : IUPAC Recommendations...
in the presence of ligands; in the presence of benzene, a fulvalene complex, μ(η5:η5-fulvalene)-di-(μ-hydrido)-bis(η5-cyclopentadienyltitanium), can be...
dioxynaphthyl unit (in green) when the fulvalene unit is oxidized by application of a current. When the fulvalene is reduced back a metastable high conductance...
Pauson, and Miller et al. Kealy and Pauson were attempting to synthesize fulvalene through the oxidation of a cyclopentadienyl salt with anhydrous FeCl3...
of dichlorocarbene. Some other notable work include the synthesis of fulvalene, the discoveries of the Doering-LaFlamme allene synthesis and the Parikh-Doering...
stabilizing ligands, the Cp2ZrII fragment is unstable and dimerizes to form a fulvalene complex. In 1954, Wilkinson and Birmingham described zirconocene dihalides...
celebrates Bill Doering's well-known nickname and was chosen to rhyme with fulvalene, a molecule of great interest to the research group. Addison Ault (2001)...
[Fe(C5H5)2], was first synthesised in 1951 during an attempt to prepare the fulvalene (C 10H 8) by oxidative dimerization of cyclopentadiene; the resultant...
Calicene or triapentafulvalene is a hydrocarbon of the fulvalene class with chemical formula C8H6, composed of a cyclopentadiene ring and a cyclopropene...
Ni(tmdt)2, Pt(tmdt)2, Pd(tmdt)2, Au(tmdt)2, The tmdt2− ion is based on fulvalene, but with the four atoms adjacent to the bridging double bond replaced...
cyclopentadienyl rings are coupled. Formally, biferrocene is derived from one fulvalene ligand, and biferrocenylene is derived from two. Biferrocene can easily...
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