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1,2-dioxetanedione

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Title: 1,2-dioxetanedione  
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Subject: Diphenyl oxalate, Bis-(2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl)oxalate, 1,2-Dioxetane, Peroxyoxalate, Oxalic anhydride, 3-Oxetanone
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1,2-dioxetanedione

1,2-Dioxetanedione
Identifiers
CAS number 26974-08-3 YesY
PubChem 14833747
ChemSpider 11535432 YesY
Jmol-3D images Image 1
Properties
Molecular formula C2O4
Molar mass 88.02 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 C2O4. It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.[1]

In ordinary conditions, it quickly decomposes to carbon dioxide (CO2) even at 180 K (−93 °C), but can be detected by mass spectrometry and other techniques.[2][3]

1,2-Dioxetanedione is an intermediate in the chemoluminescent reactions used in glowsticks.[4] The decomposition proceeds via a paramagnetic oxalate biradical intermediate.[5]

Recently it has been found that a high-energy intermediate in one of these reactions (between oxalyl chloride and hydrogen peroxide in ethyl acetate), which is presumed to be 1,2-dioxetanedione, can accumulate in solution at room temperature (up to a few micromoles at least), provided that the activating dye and all traces of metals and other reducing agents are removed from the system, and the rections are carried out in an inert atmosphere.[6]

See also

References


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