Chemistry:Benzocyclobutadiene
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| Preferred IUPAC name
Bicyclo[4.2.0]octa-1,3,5,7-tetraene | |
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3D model (JSmol)
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PubChem CID
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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). | |
 verify (what is   ?)
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| Infobox references | |
Benzocyclobutadiene is the simplest polycyclic hydrocarbon, being composed of an aromatic benzene ring fused to an anti-aromatic cyclobutadiene ring. It has chemical formula C
8H
6. 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]
Benzocyclobutadiene is used in the production of the pharmaceutical drug naflocort.[citation needed]
See also
References
- ↑ Observation of benzocyclobutadiene by flow nuclear magnetic resonance https://doi.org/10.1021/ja00168a059
- ↑ Carey, Francis A.; Sundberg, Richard J. (1984). Advanced Organic Chemistry Part A Structure and Mechanisms (2nd ed.). New York, NY: Plenum Press. ISBN 0-306-41198-9.
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