1,2-Dioxin

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).

1,2-Dioxin
Names
Preferred IUPAC name
1,2-Dioxine
Systematic IUPAC name
1,2-Dioxacyclohexa-3,5-diene
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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
C4H4O2
Molar mass 84.074 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).
N verify (what is YN ?)
Infobox references
For other dioxin compounds, see dioxin.

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

  • 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)
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