Dioxane tetraketone

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.

Dioxane tetraketone

Names
IUPAC name 1,4-Dioxane-2,3,5,6-tetrone
Identifiers
CAS Number	213967-57-8 Y
3D model (JSmol)	Interactive image
ChemSpider	8710170 N
PubChem CID	10534779
CompTox Dashboard (EPA)	DTXSID40441312
InChI InChI=1S/C4O6/c5-1-2(6)10-4(8)3(7)9-1 N Key: WBHICAWASPYOHL-UHFFFAOYSA-N N
SMILES O=C(O1)C(OC(C1=O)=O)=O
Properties
Chemical formula	C4O6
Molar mass	144.038 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.^[1] The stability and conformation of the molecule were also analyzed by theoretical methods.^[2]

See also

• 1,2-Dioxetanedione

References

1. Strazzolini, P.; Gambi, A.; Giumanini, A. G.; Vancik, H. (1998). "The reaction between ethanedioyl (oxalyl) dihalides and Ag₂C₂O₄: a route to Staudinger's elusive ethanedioic (oxalic) acid anhydride". Journal of the Chemical Society, Perkin Transactions 1. 1998 (16): 2553–2558. doi:10.1039/a803430c.
2. Gambi, A.; Guimanini, A. G.; Strazzolini, P. (2001). "Theoretical investigations on (CO)_n(CO₂)_m cyclic cooligomers". Journal of Molecular Structure: THEOCHEM. 536 (1): 9–16. doi:10.1016/S0166-1280(00)00601-1.