Malonic anhydride explained

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]}

See also

• Carbon suboxide (C₃O₂), an anhydride of malonic anhydride.
• 2-oxetanone, also called β-propiolactone
• 3-oxetanone

References

1. Cotton, F. A.; Wilkinson, G. (1988) Advanced Inorganic Chemistry, 5th edn. Wiley
2. Paradigms and Paradoxes: Aspects of the Energetics of Carboxylic Acids and Their Anhydrides. H. Mark Perks and Joel F. Liebman. Structural Chemistry . 2000. 265–269. 11. 4 . 10.1023/A:1009270411806. 92816468. 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. .