Cyclobutanetetrone

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.

Cyclobutanetetrone
Skeletal formula of cyclobutanetetrone
Names
IUPAC name
Cyclobutane-1,2,3,4-tetraone
Other names
Tetraoxocyclobutane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4O4/c5-1-2(6)4(8)3(1)7 checkY
    Key: KDAVZOLBYGNLGF-UHFFFAOYSA-N checkY
  • O=C1C(=O)C(=O)C1=O
Properties
C4O4
Molar mass 112.040 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]

Cyclobutanetetrone can be viewed as the neutral counterpart of the squarate anion C
4O2−
4, 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
  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. doi:10.1021/jz201593z. PMID 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. Bibcode:2001JPCA..105.5945J. doi:10.1021/jp010738i.
  3. Rubin, M. B.; Gleiter, R. (2000). "The Chemistry of Vicinal Polycarbonyl Compounds". Chemical Reviews. 100 (3): 1121–1164. doi:10.1021/cr960079j. PMID 11749259.
  4. Seitz, G.; Imming, P. (1992). "Oxocarbons and pseudooxocarbons". Chemical Reviews. 92 (6): 1227–1260. doi:10.1021/cr00014a004.
  5. Schröder, D.; Schwarz, H.; Dua, S.; Blanksby, S. J.; Bowie, J. H. (1999). "Mass spectrometric studies of the oxocarbons CnOn (n = 3–6)". International Journal of Mass Spectrometry. 188 (1–2): 17–25. Bibcode:1999IJMSp.188...17S. doi:10.1016/S1387-3806(98)14208-2.
  6. Cohen, S.; Lacher, J. R.; Park, J. D. (1959). "Diketocyclobutanediol". Journal of the American Chemical Society. 81 (13): 3480. doi:10.1021/ja01522a083.
  7. Skujins, S.; Delderfield, J.; Webb, G. A. (1967). "A mass spectrometric study of some monocyclic polycarbonyl compounds". Tetrahedron. 24 (13): 4805–4817. doi:10.1016/S0040-4020(01)98676-4.
  • Maahs, G.; Hegenberg, P. (2003). "Syntheses and Derivatives of Squaric Acid". Angewandte Chemie International Edition. 5 (10): 888–893. doi:10.1002/anie.196608881.

See also
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