Barrelene
Chemical compound / From Wikipedia, the free encyclopedia
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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.
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Names | |||
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Preferred IUPAC name
Bicyclo[2.2.2]octa-2,5,7-triene[1] | |||
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Properties | |||
C8H8 | |||
Molar mass | 104.15 | ||
Density | 1.013 g/mL | ||
Boiling point | 153.7 °C (308.7 °F; 426.8 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.