1,2-Dioxin

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1,2-Dioxin
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Template:Longitem Dibenzodioxin

1,4-Dioxin

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

File:Dioxin isomers.svg
1,2-Dioxin (left) and 1,4-dioxin (right)

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.[2] Even substituted derivatives, such as 1,4-diphenyl-2,3-benzodioxin, are very labile.[3]

File:1,4-diphenyl-2,3-benzodioxin.svg
Structure of the transient 1,4-diphenyl-2,3-benzodioxin

In 1990, 3,6-bis(p-tolyl)-1,2-dioxin (1) was incorrectly reported as the first stable derivative.[4] It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable dione (2).[5]

File:Revised structure 1,2-Dioxin.svg
Dioxin (1) and dione form (2)

References

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