Benzocyclobutadiene is the simplest polycyclic hydrocarbon, being composed of an aromatic benzene ring fused to an anti-aromatic cyclobutadiene ring. It has chemical formula C8H6. Though the benzene ring is stabilized by aromaticity, the cyclobutadiene portion has a destabilizing effect. This results into it being a non-aromatic compound - neither behaving as aromatic nor an antiaromatic one.[1] For this reason, benzocyclobutadiene will readily dimerize or polymerize and it reacts as a dienophile in Diels-Alder reactions.[2]
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Preferred IUPAC name
Bicyclo[4.2.0]octa-1,3,5,7-tetraene | |
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Properties | |
C8H6 | |
Molar mass | 102.136 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Benzocyclobutadiene is used in the production of the pharmaceutical drug naflocort.[citation needed]