Cyclopropanetrione Explained

Cyclopropanetrione or trioxocyclopropane is a little-known oxide of carbon with formula C₃O₃. It consists of a ring of three carbon atoms each attached to an oxygen atom with a double bond. Alternately, it can be thought as a trimer of carbon monoxide. This compound is thermodynamically unstable and has not been produced in bulk.^[1] However, it has been detected using mass spectrometry.^{[2] [3]}

It is the neutral equivalent of the deltate anion C₃O₃²⁻, known since 1975.^[4] An equivalent hydrate hexahydroxycyclopropane or cyclopropane-1,1,2,2,3,3-hexol, (-C(OH)₂-)₃ also exists. This contains geminal hydroxy groups.^[5]

References

1. Corkran. Greg. David W. Ball. 2004. The relative energies of cyclopropanone, cyclopropanedione, and cyclopropanetrione. Hartree–Fock, density-functional, G2, and CBS calculations. Journal of Molecular Structure: THEOCHEM. 668. 2–3. 171–178. 0166-1280. 10.1016/j.theochem.2003.10.026.
2. Schröder. Detlef. Helmut Schwarz . Suresh Dua . Stephen J. Blanksby . John H. Bowie . 1999. Mass spectrometric studies of the oxocarbons CnOn (n = 3–6). International Journal of Mass Spectrometry. 188. 1–2. 17–25. 1387-3806. 10.1016/S1387-3806(98)14208-2. 1999IJMSp.188...17S.
3. Eggerding. David. Robert West. 1975. Synthesis of dihydroxycyclopropenone (deltic acid). Journal of the American Chemical Society. 97. 1. 207–208. 0002-7863. 10.1021/ja00834a047.
4. Eggerding. David. Robert West. 1976. Synthesis and properties of deltic acid (dihydroxycyclopropenone) and the deltate ion. Journal of the American Chemical Society. 98. 12. 3641–3644. 0002-7863. 10.1021/ja00428a043.
5. Skujins. S.. J. Delderfield, G.A. Webb. 1968. A mass spectrometric study of some monocyclic polycarbonyl compounds. Tetrahedron. 24. 13. 4805–4817. 0040-4020. 10.1016/S0040-4020(01)98676-4.