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1,2-Dioxetanedione

The chemical compound 1,2-dioxetanedione, or 1,2-dioxacyclobutane-3,4-dione, often called peroxyacid ester, is an unstable oxide of carbon (an oxocarbon) with formula CO. It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.

In ordinary conditions, it quickly decomposes to carbon dioxide (CO) even at 180 K, but can be detected by mass spectrometry and other techniques.

1,2-Dioxetanedione is an intermediate in the chemoluminescent reactions used in glowsticks. The decomposition proceeds via a paramagnetic oxalate biradical intermediate.

It is an intermediate in a reaction (between oxalyl chloride and hydrogen peroxide in ethyl acetate, accumulating in solution at room temperature up to a few micromoles, provided that the activating dye and all traces of metals and other reducing agents are removed from the system, and the reactions are carried out in an inert atmosphere.

References

References

  1. Alfred Hassner (1985): Chemistry of Heterocyclic Compounds: Small Ring Heterocycles, Part 3: Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others, Volume 42. {{ISBN. 978-0-471-05624-9 {{ISBN. 978-0-470-18720-3 John Wiley & Sons.
  2. J. Stauff. (1972). "Chemilumineszenz des "Dioxetandions"". Z. Naturforsch..
  3. (March 2018). "Chemi- and Bioluminescence of Cyclic Peroxides". Chemical Reviews.
  4. Richard Bos. (2009). "In Search of a Chemiluminescence 1,4-Dioxy Biradical". J. Am. Chem. Soc..
  5. Luiz F. M. L. Ciscato, Fernando H. Bartoloni, Erick L. Bastos, and Wilhelm J. Baader (2009), ''Direct Kinetic Observation of the Chemiexcitation Step in Peroxyoxalate Chemiluminescence''. Journal of Organic Chemistry, volume 74, 8974–8979. {{doi. 10.1021/jo901402k.
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oxocarbons lactones dioxetanes organic-peroxides chemiluminescence conjugated-ketones
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