Fulvene (pentafulvene) is a
hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
with the formula (CH=CH)
2C=CH
2. It is a prototype of a
cross-conjugated Cross-conjugation is a special type of conjugation in a molecule, when in a set of three pi bonds only two pi bonds interact with each other by conjugation, while the third one is excluded from interaction.
Whereas a normal conjugated system such ...
hydrocarbon. Fulvene is rarely encountered, but substituted derivatives (
fulvenes
Fulvenes are the class of hydrocarbon obtained by formally cross-conjugation, cross-conjugating one Cycloalkane, ring and methylidene through a common exocyclic alkene, double bond.
The name is derived from fulvene, which has one pentagonal ring. ...
) are numerous. They are mainly of interest as
ligand
In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...
s and precursors to ligands in
organometallic chemistry
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and so ...
.
Fulvene is an isomer of
benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
, which when irradiated at 237 to 254 nm forms small amounts of fulvene along with
benzvalene
Benzvalene is an organic compound and one of several isomers of benzene. It was first synthesized in 1967 by K. E. Wilzbach et al. via photolysis of benzene and the synthesis was later improved by Thomas J. Katz et al.
The 1971 synthesis consist ...
.
See also
*
Fulvalene
Fulvalene (bicyclopentadienylidene) is the member of the fulvalene family 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 mor ...
*
Methylenecyclopropene
3-Methylenecyclopropene, also called methylenecyclopropene or triafulvene, is a hydrocarbon with chemical formula . It is a colourless gas that polymerizes readily as a liquid or in solution but is stable as a gas.W. E. Billups , Long Jin Lin , Ed ...
References
{{Authority control
Hydrocarbons
Vinylidene compounds
Cyclopentadienes