1,2-Dioxin

1,2-Dioxin
Names
	Systematic IUPAC name 1,2-Dioxine[1]
Identifiers
CAS Number	289-87-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	10606250 ;
PubChem CID	15559065;
	InChI InChI=1S/C4H4O2/c1-2-4-6-5-3-1/h1-4H Key: VCZQYTJRWNRPHF-UHFFFAOYSA-N ; InChI=1/C4H4O2/c1-2-4-6-5-3-1/h1-4H Key: VCZQYTJRWNRPHF-UHFFFAOYAH;
	SMILES O1OC=CC=C1;
Properties
Chemical formula	C4H4O2
Molar mass	84.07 g·mol−1
Related compounds
Related compounds	Dibenzodioxin; 1,4-Dioxin
	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

1,2-Dioxin is a heterocyclic, organic, antiaromatic compound with the chemical formula C₄H₄O₂. It is an isomeric form of 1,4-dioxin (or p-dioxin).

Due to its peroxide-like characteristics, 1,2-dioxin is very unstable and has not been isolated. Even substituted derivatives are very labile, e.g. 1,4-diphenyl-2,3-benzodioxin.^[2] Indeed, in 1990, 3,6-bis(p-tolyl)-1,2-dioxin was wrongly accounted as the first stable derivative.^[3] It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable dione.^[4]

The isomers 1,2-dioxin (left) and 1,4-dioxin (right)
Structure of the transient 1,4-diphenyl- 2,3-benzodioxin
Dioxin (1) and dione form (2)

References

↑ "CID 15559065 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 12 February 2002. Identification and Related Records. Retrieved 7 October 2011.
↑ Smith, Jimmie P.; Schrock, Alan K.; Schuster, Gary B. (1982). "Chemiluminescence of organic peroxides. Thermal generation of an o-xylylene peroxide". Journal of the American Chemical Society. 104 (4): 1041. doi:10.1021/ja00368a021. .
↑ Shine, Henry J.; Zhao, Da Chuan (1990). "Electron transfer to excited doublet states. Photoirradiation of 10-methylphenothiazine cation radical perchlorate in solutions of phenylacetylene and p-tolylacetylene in acetonitrile". The Journal of Organic Chemistry. 55 (13): 4086. doi:10.1021/jo00300a026. .
↑ Block, Eric; Shan, Zhixing; Glass, Richard S.; Fabian, Jürgen (2003). "Revised Structure of a Purported 1,2-Dioxin: A Combined Experimental and Theoretical Study". The Journal of Organic Chemistry. 68 (10): 4108. doi:10.1021/jo034305i. PMID 12737603.

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[1] "CID 15559065 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 12 February 2002. Identification and Related Records. Retrieved 7 October 2011.

[2] Smith, Jimmie P.; Schrock, Alan K.; Schuster, Gary B. (1982). "Chemiluminescence of organic peroxides. Thermal generation of an o-xylylene peroxide". Journal of the American Chemical Society. 104 (4): 1041. doi:10.1021/ja00368a021. .

[3] Shine, Henry J.; Zhao, Da Chuan (1990). "Electron transfer to excited doublet states. Photoirradiation of 10-methylphenothiazine cation radical perchlorate in solutions of phenylacetylene and p-tolylacetylene in acetonitrile". The Journal of Organic Chemistry. 55 (13): 4086. doi:10.1021/jo00300a026. .

[4] Block, Eric; Shan, Zhixing; Glass, Richard S.; Fabian, Jürgen (2003). "Revised Structure of a Purported 1,2-Dioxin: A Combined Experimental and Theoretical Study". The Journal of Organic Chemistry. 68 (10): 4108. doi:10.1021/jo034305i. PMID 12737603.