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- Barrelene abstract "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 H. E. Zimmerman in 1960 the name derives from the obvious 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. Like benzene, barrelene has a set of 6 cyclic, but not planar, overlapping p-orbitals. Because of overlap of opposite-sign lobes, the structure represents Möbius aromaticity.Barrelene with set of p-orbitalsTriptycenes, with the alkene groups part of an arene, are related compounds. It is also a starting material for many other organic compounds such as semibullvalene.The original Zimmerman synthesis modified in 1969 starts from coumalic acid:Barrelene Synthesis Zimmermann 1969many alternative routes have been devised since then, one of them starting from oxepin: Barrelene Synthesis 1997An alternate route that allows synthesis of the parent barrelene system and a variety of substituted barrelenes has also been reportedSubstituted Barrelene Synthesis".
- Barrelene iupacName "Bicyclo[2.2.2]octa-2,5,7-triene".
- Barrelene thumbnail Barrelene_structure.png?width=300.
- Barrelene wikiPageID "5292881".
- Barrelene wikiPageRevisionID "602092156".
- Barrelene hasPhotoCollection Barrelene.
- Barrelene imagefilel "Barrelene structure.png".
- Barrelene imagefiler "Barrelene 3D.png".
- Barrelene iupacname "Bicyclo[2.2.2]octa-2,5,7-triene".
- Barrelene verifiedrevid "410628703".
- Barrelene watchedfields "changed".
- Barrelene subject Category:Alkenes.
- Barrelene type Abstraction100002137.
- Barrelene type AliphaticCompound114601294.
- Barrelene type Alkene114713120.
- Barrelene type Alkenes.
- Barrelene type Chemical114806838.
- Barrelene type Compound114818238.
- Barrelene type Material114580897.
- Barrelene type Matter100020827.
- Barrelene type OrganicCompound114727670.
- Barrelene type Part113809207.
- Barrelene type PhysicalEntity100001930.
- Barrelene type Relation100031921.
- Barrelene type Substance100019613.
- Barrelene type ChemicalCompound.
- Barrelene type ChemicalSubstance.
- Barrelene type ChemicalSubstanceType.
- Barrelene type ChemicalObject.
- Barrelene type Thing.
- Barrelene comment "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 H. E. Zimmerman in 1960 the name derives from the obvious 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.".
- Barrelene label "Barreleen".
- Barrelene label "Barrelene".
- Barrelene label "Barrelene".
- Barrelene label "桶烯".
- Barrelene sameAs Barrelene.
- Barrelene sameAs Barreleen.
- Barrelene sameAs m.0dc_hy.
- Barrelene sameAs Q653667.
- Barrelene sameAs Q653667.
- Barrelene sameAs Barrelene.
- Barrelene wasDerivedFrom Barrelene?oldid=602092156.
- Barrelene depiction Barrelene_structure.png.
- Barrelene isPrimaryTopicOf Barrelene.