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1,3-Dioxetane

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1,3-Dioxetane
Names
Preferred IUPAC name 1,3-Dioxetane
Systematic IUPAC name 1,3-Dioxacyclobutane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H4O2/c1-3-2-4-1/h1-2H2Key: GFAJOMHUNNCCJQ-UHFFFAOYSA-N
  • InChI=1/C2H4O2/c1-3-2-4-1/h1-2H2Key: GFAJOMHUNNCCJQ-UHFFFAOYAT
SMILES
  • C1OCO1
  • O1COC1
Properties
Chemical formula C2H4O2
Molar mass 60.052 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

1,3-Dioxetane (1,3-dioxacyclobutane) is a heterocyclic organic compound with formula C2O2H4, whose backbone is a four-member ring of alternating oxygen and carbon atoms. It can be viewed as a dimer of formaldehyde (COH2).

Derivatives of 1,3-dioxetane are rarely encountered as intermediates in the literature. Usually, they are prepared via cycloadditions of two carbonyl compounds. Molecular orbital theory calculations suggest that they should be more stable than the 1,2-isomers, which are more intensively studied.

See also

References

  1. Cordier, C.; Leach, S.; Nelson, A. (2014). Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 29: Acetals: Hal/X and O/O, S, Se, Te. Georg Thieme Verlag. p. 407. ISBN 9783131720412.


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