Benzocyclobutadiene

Benzocyclobutadiene
Names
	Preferred IUPAC name Bicyclo[4.2.0]octa-1,3,5,7-tetraene
Identifiers
CAS Number	4026-23-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	70373 ;
PubChem CID	77987;
UNII	T7CEM83V4M ;
CompTox Dashboard (EPA)	DTXSID60193245 ;
	InChI InChI=1S/C8H6/c1-2-4-8-6-5-7(8)3-1/h1-6H Key: WHEATZOONURNGF-UHFFFAOYSA-N ; InChI=1/C8H6/c1-2-4-8-6-5-7(8)3-1/h1-6H Key: WHEATZOONURNGF-UHFFFAOYAK;
	SMILES C12=CC=CC=C1C=C2;
Properties
Chemical formula	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 ?) 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 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]}

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.

[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.

[1]

[2]

See also

References