1,2-Dioxetanedione

changed changed 477204215 1,2-Dioxetanedione.svg File:Chemfm 1 2 dioxetanedione.svg 120px 1,2-Dioxetanedione Peroxyacid ester WYNZXNXFHYJUTE-UHFFFAOYAI correct chemspider 1S/C2O4/c3-1-2(4)6-5-1 correct chemspider WYNZXNXFHYJUTE-UHFFFAOYSA-N changed ?? 26974-08-3 14833747 correct chemspider 11535432 O=C1OOC1=O 1/C2O4/c3-1-2(4)6-5-1 2 4 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.Alfred Hassner (1985): Chemistry of Heterocyclic Compounds: Small Ring Heterocycles, Part 3: Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others, Volume 42. 978-0-471-05624-9 978-0-470-18720-3 John Wiley & Sons. In ordinary conditions, it quickly decomposes to carbon dioxide (CO2) even at 180 K C 3, but can be detected by mass spectrometry and other techniques.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 10.1021/ja01053a065 1969JAChS..91.7209C Chemilumineszenz des "Dioxetandions" Chemiluminescence of „Dioxetanedione“ J. Stauff W. Jaeschke G. Schlögl 1972 Z. Naturforsch. B 27 11 1434–1435 10.1515/znb-1972-1140 94708095 free https://publikationen.ub.uni-frankfurt.de/files/76112/10.1515_znb-1972-1140.pdfJune 2026 InternetArchiveBot 1,2-Dioxetanedione is an intermediate in the chemoluminescent reactions used in glowsticks.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 Chemi- and Bioluminescence of Cyclic Peroxides Chemical Reviews 118 15 6927–6974 March 2018 10.1021/acs.chemrev.7b00649 29493234 2018ChRv..118.6927V 10550/106201 free Richard Bos Neil W. Barnett Gail A. Dyson Kieran F. Lim Richard A. Russell Simon P. Watson amp 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 10.1016/j.aca.2003.10.014 141–147 The decomposition proceeds via a paramagnetic oxalate biradical intermediate. Richard Bos Sarah A. Tonkin Graeme R. Hanson Christopher M. Hindson Kieran F. Lim Neil W. Barnett amp 2009 In Search of a Chemiluminescence 1,4-Dioxy Biradical J. Am. Chem. Soc. 131 8 2770–2771 10.1021/ja808401p 19206238 2009JAChS.131.2770B 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.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. 10.1021/jo901402k. See also 1,3-dioxetanedione References External links Category:Oxocarbons Category:Lactones Category:Dioxetanes Category:Organic peroxides Category:Chemiluminescence Category:Conjugated ketones