出典:Wikipedia
出典:『Wikipedia』 (2011/01/28 20:43 UTC 版)
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 with 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 it is not possible to avoid a destabilizing overlap of opposite-sign lobes, the structure represents Möbius aromaticity.