Cyclobutanetetrone

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Cyclobutanetetrone
Skeletal formula of cyclobutanetetrone
Identifiers
CAS number 3617-57-0 N
ChemSpider 24735246 YesY
Jmol-3D images Image 1
Properties
Molecular formula C4O4
Molar mass 112.04 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Cyclobutanetetrone, also called tetraoxocyclobutane, is an organic compound[1] with formula C4O4 or (-(C=O)-)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[edit]

Cyclobutanetetrone can be viewed as the neutral counterpart of the squarate anion C4O42−, which is stable and has been known at least since 1959.[6]

The compound octahydroxycyclobutane or cyclobutane-1,1,2,2,3,3,4,4-octaol (-C(OH)2-)4 may be referred to in the literature as "hydrated tetraoxocyclobutane".[7]

References[edit]

  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. 
  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. 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. 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[edit]