Malonic anhydride
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Oxetane-2,4-dione
Other names
Malonic anhydride
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C3H2O3/c4-2-1-3(5)6-2/h1H2 checkY
    Key: KKHUSADXXDNRPW-UHFFFAOYSA-N checkY
  • InChI=1/C3H2O3/c4-2-1-3(5)6-2/h1H2
    Key: KKHUSADXXDNRPW-UHFFFAOYAB
  • O=C1OC(=O)C1
Properties
C3H2O3
Molar mass 86.046 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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): 265–269. doi:10.1023/A:1009270411806. ISSN 1040-0400. S2CID 92816468.
  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

Categories