1,2-Dioxin

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1,2-Dioxin
Systematic name

1,2-Dioxine[1]

Identifiers
CAS number 289-87-2 N
PubChem 15559065
ChemSpider 10606250 YesY
Jmol-3D images Image 1
Properties
Molecular formula C4H4O2
Molar mass 84.07 g mol−1
Related compounds
Related compounds Dibenzodioxin

1,4-Dioxin

 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 could not be isolated. Even substituted derivatives are very labile, e.g. 1,4-diphenyl-2,3-benzodioxin.[2] In 1990, 3,6-bis(p-tolyl)-1,2-dioxin was wrongly accounted for the first stable derivative.[3] It could be shown that the 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

  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. ↑ J. P. Smith, A. K. Schrock, G. B. Schuster: Chemiluminescence of organic peroxides. Thermal generation of an o-xylylene peroxide, J. Am. Chem. Soc., 1981, 104, 1041–1047; doi:10.1021/ja00368a021.
  3. ↑ H. J. Shine, D. C. Zhao: Electron transfer to excited doublet states. Photoirradiation of 10-methylphenothiazine cation radical perchlorate in solutions of phenylacetylene and p-tolylacetylene in acetonitrile, J. Org. Chem., 1990, 55, 4086–4089; doi:10.1021/jo00300a026.
  4. ↑ E. Block, Z. Shan, R. S. Glass, J. Fabian: Revised structure of a purported 1,2-dioxin: a combined experimental and theoretical study, J. Org. Chem., 2003, 68, 4108–4111; PMID 12737603; doi:10.1021/jo034305i.


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