Dioxane tetraketone

Dioxane tetraketone
IUPAC name 1,4-Dioxane-2,3,5,6-tetrone
Identifiers
CAS number	213967-57-8
Jmol-3D images	Image 1
SMILES O=C(O1)C(OC(C1=O)=O)=O
Properties
Molecular formula	C4O6
Molar mass	144.04 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

References

1. ^ Paolo Strazzolini, Alberto Gambi, Angelo G. Giumanini and Hrvoj Vancik (1998). "The reaction between ethanedioyl (oxalyl) dihalides and Ag₂C₂O₄: a route to Staudinger’s elusive ethanedioic (oxalic) acid anhydride". J. Chem. Soc., Perkin Trans. 1 (16): 2553–2558. doi:10.1039/a803430c. 
2. ^ Alberto Gambi, Angelo G. Guimanini, and Paolo Strazzolini (2001), Theoretical investigations on (CO)_n(CO₂)_m cyclic cooligomers. Journal of Molecular Structure: THEOCHEM, Volume 536, Issue 1, Pages 9–16 doi:10.1016/S0166-1280(00)00601-1

See also

• 1,2-Dioxetanedione