Benzocyclobutadiene
Appearance
Names | |
---|---|
Preferred IUPAC name
Bicyclo[4.2.0]octa-1,3,5,7-tetraene | |
Identifiers | |
3D model (JSmol)
|
|
ChemSpider | |
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
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).
|
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]
Benzocyclobutadiene is used in the production of the pharmaceutical drug naflocort.[citation needed]
See also
[edit]References
[edit]- ^ 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.