Benzocyclobutadiene

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]

Not to be confused with benzocyclobutene.
Benzocyclobutadiene
Names
Preferred IUPAC name
Bicyclo[4.2.0]octa-1,3,5,7-tetraene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C8H6/c1-2-4-8-6-5-7(8)3-1/h1-6H Y
    Key: WHEATZOONURNGF-UHFFFAOYSA-N Y
  • InChI=1/C8H6/c1-2-4-8-6-5-7(8)3-1/h1-6H
    Key: WHEATZOONURNGF-UHFFFAOYAK
  • C12=CC=CC=C1C=C2
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).
Y verify (what is YN ?)
Infobox references

Benzocyclobutadiene is used in the production of the pharmaceutical drug naflocort.

See also

References
  1. Observation of benzocyclobutadiene by flow nuclear magnetic resonance https://doi.org/10.1021/ja00168a059
  2. 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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