1,2-Dioxin

Names

Systematic IUPAC name

1,2-Dioxine^[1]

Identifiers

CAS Number

289-87-2^N

3D model (Jmol)

10606250^Y

InChI=1S/C4H4O2/c1-2-4-6-5-3-1/h1-4H^Y
Key: VCZQYTJRWNRPHF-UHFFFAOYSA-N^Y
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

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.
↑ 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.
↑ 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.
↑ 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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