The
chemicalcompound1,2-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 (−93.1 °C), but can be detected by
mass spectrometry and other techniques.[2][3]
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 reactions are carried out in an inert atmosphere.[7]
^Alfred Hassner (1985): Chemistry of Heterocyclic Compounds: Small Ring Heterocycles, Part 3: Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others, Volume 42.
ISBN978-0-471-05624-9ISBN978-0-470-18720-3 John Wiley & Sons.
^Herman F. Cordes; Herbert P. Richter; Carl A. Heller (1969). "Mass spectrometric evidence for the existence of 1,2-dioxetanedione (carbon dioxide dimer). Chemiluminescent intermediate". J. Am. Chem. Soc. 91 (25): 7209.
doi:
10.1021/ja01053a065.
^Vacher, Morgane; Fdez. Galván, Ignacio; Ding, Bo-Wen; Schramm, Stefan; Berraud-Pache, Romain; Naumov, Panče; Ferré, Nicolas; Liu, Ya-Jun; Navizet, Isabelle; Roca-Sanjuán, Daniel; Baader, Wilhelm J.; Lindh, Roland (March 2018). "Chemi- and Bioluminescence of Cyclic Peroxides". Chemical Reviews. 118 (15): 6927–6974.
doi:
10.1021/acs.chemrev.7b00649.
PMID29493234.
^Richard Bos; Neil W. Barnett; Gail A. Dyson; Kieran F. Lim; Richard A. Russell & Simon P. Watson (2003). "Studies on the mechanism of the peroxyoxalate chemiluminescence reaction: Part 1. Confirmation of 1,2-dioxetanedione as an intermediate using 13C nuclear magnetic resonance spectroscopy". Analytica Chimica Acta. 502 (2): 141–147.
doi:
10.1016/j.aca.2003.10.014.
^Richard Bos; Sarah A. Tonkin; Graeme R. Hanson; Christopher M. Hindson; Kieran F. Lim & Neil W. Barnett (2009). "In Search of a Chemiluminescence 1,4-Dioxy Biradical". J. Am. Chem. Soc. 131 (8): 2770–2771.
doi:
10.1021/ja808401p.
PMID19206238.
^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.