Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Barrelene is a bicyclic organic compound with chemical formula C8H8 and systematic name bicyclo[2.2.2]octa-2,5,7-triene. First synthesized and described by Howard Zimmerman in 1960, the name derives from the resemblance to a barrel, with the staves being three ethylene units attached to two methine groups. It is the formal Diels–Alder adduct of benzene and acetylene. Due to its unusual molecular geometry, the compound is of considerable interest to theoretical chemists.
Iptycenes, with the alkene groups part of an arenes, are related compounds. It is also a starting material for many other organic compounds, such as semibullvalene.
^International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1257. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
Barrelene is a bicyclic organic compound with chemical formula C8H8 and systematic name bicyclo[2.2.2]octa-2,5,7-triene. First synthesized and described...
The molecular formula C8H8 may refer to: Barrelene Benzocyclobutene (BCB) Cubane Cuneane Cyclooctatetraene Semibullvalene Polystyrene Styrene Xylylene...
replaced by a single bond. The compound was first prepared by photolysis of barrelene in isopentane with acetone as a photosensitizer in 1966. Semibullvalene...
Howard E.; Robert M. Paufler (1960). "Bicyclo [2.2.2]octa-2,5,7-triene (barrelene), a unique cyclic six electron pi system". Journal of the American Chemical...
with chemical yields near 90%: COT can also be prepared by photolysis of barrelene, one of its structural isomers, the reaction proceeding via another isolable...
Wagner, M. (2014). "Insertion Reactions into the Boron–Boron Bonds of Barrelene-Type 1,2-Diaminodiboranes(4)". Organometallics. 33 (23): 6967–6974. doi:10...
bridged bicyclo-octatriene core structure. They are formally derivatives of barrelene. The first and simplest iptycene molecule is triptycene. The first iptycene...
of the molecule.: xi Some are pictured below. Other examples include barrelene (shaped like a barrel),: 58 fenestrane (having a window-pane motif),: 55 ...
3-dimethyl-1,4-pentadiene (the "Mariano" molecule) and the rearrangement of barrelene to semibullvalene. We note that, in contrast to the cyclohexadienone reactions...
L. A.; Cabeza, J. A. (1985). "Dinuclear Methoxy, Cyclooctadiene, and Barrelene Complexes of Rhodium(I) and Iridium(I)". Inorganic Syntheses. Vol. 23...
the best examples of neutral homoaromatics are bishomoaromatics such as barrelene and semibullvalene. First synthesized in 1966, semibullvalene has a structure...
three-piece art panel, the triptych. Several substituted triptycenes are known. Barrelenes are structurally related. Due to the rigid framework and three-dimensional...
Mariano, P. S. J. Am. Chem. Soc., 1969, 91, 1718-1727. ISSN 0002-7863 "The Barrelene to Semibullvalene Transformation. Correlation of Excited State Potential...
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