1,3-Dioxetane

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).

1,3-Dioxetane
Names
Preferred IUPAC name
1,3-Dioxetane
Systematic IUPAC name
1,3-Dioxacyclobutane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C2H4O2/c1-3-2-4-1/h1-2H2 checkY
    Key: GFAJOMHUNNCCJQ-UHFFFAOYSA-N checkY
  • InChI=1/C2H4O2/c1-3-2-4-1/h1-2H2
    Key: GFAJOMHUNNCCJQ-UHFFFAOYAT
  • C1OCO1
  • O1COC1
Properties
C2H4O2
Molar mass 60.052 g·mol−1
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

Derivatives of 1,3-dioxetane are rarely encountered as intermediates in the literature. Usually, they are prepared via [2+2] 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.[1]

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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