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1,2-Dioxin

1,4-Dioxin

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

:[[File:Dioxin isomers.svg|thumb|left|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. Even substituted derivatives, such as 1,4-diphenyl-2,3-benzodioxin, are very labile.

:[[File:1,4-diphenyl-2,3-benzodioxin.svg|thumb|left|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. It was subsequently shown that the initial compound was not a derivative of 1,2-dioxin, but a thermodynamically more stable dione (2).

:[[File:Revised structure 1,2-Dioxin.svg|thumb|left|Dioxin (1) and dione form (2)]]

References

References

  1. (2013-09-01). "Parity violation energies of C4H4X2 molecules for X = O, S, Se, Te and Po". Molecular Physics.
  2. Matsumoto, M.. (2014). "Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 16: Six-Membered Hetarenes with Two Identical Heteroatoms". Georg Thieme Verlag.
  3. (1982). "Chemiluminescence of organic peroxides. Thermal generation of an o-xylylene peroxide". Journal of the American Chemical Society.
  4. (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.
  5. (2003). "Revised Structure of a Purported 1,2-Dioxin: A Combined Experimental and Theoretical Study". The Journal of Organic Chemistry.
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dioxins hypothetical-chemical-compounds antiaromatic-compounds
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