Malonic anhydride

Malonic anhydride
Names
IUPAC name
Oxetane-2,4-dione
Other names
Malonic anhydride
Identifiers
ChemSpider 8351595 Yes
Jmol-3D images Image
PubChem 10176090
Properties
Molecular formula
 C3H2O3
Molar mass 86.05 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Malonic anhydride or oxetane-2,4-dione is an organic compound with chemical formula C3H2O3 or CH2(CO)2O. It can be viewed as the anhydride of malonic acid, or a double ketone of oxetane.

Malonic anhydride was first synthesized in 1988 by ozonolysis of diketene.[1][2] Some derivatives, such as 3,3-dimethyl-oxetane-2,4-dione, are known.[3][4][5]

References

  1. ↑ Cotton, F. A.; Wilkinson, G. (1988) Advanced Inorganic Chemistry, 5th edn. Wiley
  2. ↑ H. Mark Perks and Joel F. Liebman (2000). "Paradigms and Paradoxes: Aspects of the Energetics of Carboxylic Acids and Their Anhydrides". Structural Chemistry 11 (4): 265269. doi:10.1023/A:1009270411806. ISSN 1040-0400.
  3. ↑ Charles L. Perrin; Arrhenius, T (1978). J. Am. Chem. SOC. volume 100, pages 5249-5251.
  4. ↑ Ribeiro da Silva, M. A. J.; Monte, M. J. S.; Ribeiro, J. R.(1999) J. Chem.Thermodyn. 31, 1093.
  5. ↑ Charles L. Perrin, Douglas Magde, Sylvia J. Berens, Julie Roque (1980), Raman spectrum of a malonic anhydride. (Actually, of 3,3-dimethyl-oxetane-2,4-dione.) J. Org. Chem., volume 45 issue 9, pp 1705–1706. doi:10.1021/jo01297a044.

See also