Cyclobutanetetrone Explained

Cyclobutanetetrone, also called tetraoxocyclobutane, is an organic compound^[1] with formula C₄O₄ or (CO)₄, the fourfold ketone of cyclobutane. It would be an oxide of carbon, indeed a tetramer of carbon monoxide.

The compound seems to be thermodynamically unstable.^[2] As of 2000, it had yet to be synthesized in significant amounts^{[3] [4]} but may have transient existence as detected by mass spectrometry.^[5]

Related compounds

Cyclobutanetetrone can be viewed as the neutral counterpart of the squarate anion, which is stable and has been known at least since 1959.^[6]

The compound octahydroxycyclobutane or cyclobutaneoctaol (C(OH)₂)₄ may be referred to in the literature as "hydrated tetraoxocyclobutane".^[7]

References

• Maahs . G. . Hegenberg . P. . 2003 . Syntheses and Derivatives of Squaric Acid . Angewandte Chemie International Edition . 5 . 10 . 888–893 . 10.1002/anie.196608881 .

See also

• Cyclohexanehexone
• Cyclopentanepentone

Notes and References

1. Guo . J.-C. . Hou . G.-L. . Li . S.-D. . Wang . X.-B. . 2012 . Probing the Low-Lying Electronic States of Cyclobutanetetraone (C₄O₄) and Its Radical Anion: A Low-Temperature Anion Photoelectron Spectroscopic Approach. Journal of Physical Chemistry A . 3 . 3 . 304–308 . 10.1021/jz201593z. 26285843 .
2. Jiao . H. . Frapper . G. . Halet . J.-F. . Saillard . J.-Y. . 2001 . Stability of Tetraoxocyclobutane Revised: Perturbation Theory and Density Functional Scheme . Journal of Physical Chemistry Letters . 105 . 24 . 5945–5947 . 10.1021/jp010738i . 2001JPCA..105.5945J .
3. Rubin . M. B. . Gleiter . R. . 2000 . The Chemistry of Vicinal Polycarbonyl Compounds . Chemical Reviews . 100 . 3 . 1121–1164 . 10.1021/cr960079j . 11749259.
4. Oxocarbons and pseudooxocarbons . Seitz . G. . Imming . P. . Chemical Reviews . 1992 . 92 . 6 . 1227–1260 . 10.1021/cr00014a004 .
5. Mass spectrometric studies of the oxocarbons C_nO_n (n = 3–6) . Schröder . D. . Schwarz . H. . Dua . S. . Blanksby . S. J. . Bowie . J. H. . 10.1016/S1387-3806(98)14208-2 . International Journal of Mass Spectrometry . 188 . 1–2 . 1999 . 17–25 . 1999IJMSp.188...17S .
6. Cohen . S. . Lacher . J. R. . Park . J. D. . Diketocyclobutanediol . Journal of the American Chemical Society . 1959 . 81 . 13 . 3480 . 10.1021/ja01522a083 .
7. Skujins . S. . Delderfield . J. . Webb . G. A. . A mass spectrometric study of some monocyclic polycarbonyl compounds . Tetrahedron . 1967 . 24 . 13 . 4805–4817 . 10.1016/S0040-4020(01)98676-4 .