dioxane tetraketone

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| ImageFileL1 = File:Dioxane-tetraketone-3D-balls.png

| ImageFileR1 = Dioxane-tetraketone-3D-spacefill.png

| ImageAlt1 = Dioxane tetraketone molecule

| IUPACName = 1,4-Dioxane-2,3,5,6-tetrone

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| CASNo = 213967-57-8

| PubChem = 10534779

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| ChemSpiderID = 8710170

| SMILES = O=C(O1)C(OC(C1=O)=O)=O

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| StdInChI = 1S/C4O6/c5-1-2(6)10-4(8)3(7)9-1

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| StdInChIKey = WBHICAWASPYOHL-UHFFFAOYSA-N

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| C=4 | O=6

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Dioxane tetraketone (or 1,4-dioxane-2,3,5,6-tetrone) is an organic compound with the formula C₄O₆. It is an oxide of carbon (an oxocarbon), which can be viewed as the fourfold ketone of dioxane. It can also be viewed as the cyclic dimer of oxiranedione (C₂O₃), the hypothetical anhydride of oxalic acid.

In 1998, Paolo Strazzolini and others synthesized this compound by reacting oxalyl chloride (COCl)₂ or the bromide (COBr)₂ with a suspension of silver oxalate (Ag₂C₂O₄) in diethyl ether at −15 °C, followed by evaporation of the solvent at low temperature and pressure. The substance is stable when dissolved in ether and trichloromethane at −30 °C, but decomposes into a 1:1 mixture of carbon monoxide (CO) and carbon dioxide (CO₂) upon heating to 0 °C.{{ cite journal | title = The reaction between ethanedioyl (oxalyl) dihalides and Ag₂C₂O₄: a route to Staudinger's elusive ethanedioic (oxalic) acid anhydride |author1=Strazzolini, P. |author2=Gambi, A. |author3=Giumanini, A. G. |author4=Vancik, H. | journal = Journal of the Chemical Society, Perkin Transactions 1 | year = 1998 | volume = 1998 | issue = 16 | pages = 2553–2558 | doi = 10.1039/a803430c }} The stability and conformation of the molecule were also analyzed by theoretical methods.{{ cite journal |author1=Gambi, A. |author2=Guimanini, A. G. |author3=Strazzolini, P. | year = 2001 | title = Theoretical investigations on (CO)_n(CO₂)_m cyclic cooligomers | journal =Journal of Molecular Structure: THEOCHEM | volume = 536 | issue = 1 | pages = 9–16 | doi = 10.1016/S0166-1280(00)00601-1 }}