Malonic anhydride or oxetane-2,4-dione is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with
chemical formula
In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbol ...
C
3H
2O
3 or CH
2(CO)
2O. It can be viewed as the
anhydride
An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the pa ...
of
malonic acid
Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid' ...
, or a double
ketone of
oxetane
Oxetane, or 1,3-propylene oxide, is a heterocyclic organic compound with the molecular formula , having a four-membered ring with three carbon atoms and one oxygen atom.
The term "an oxetane" or "oxetanes" refer to any organic compound containing ...
.
Malonic anhydride was first synthesized in 1988 by
ozonolysis
In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds of alkenes (), alkynes (), or azo compounds () are cleaved with ozone (). Alkenes and alkynes form organic compounds in which the multiple carbon–carbon b ...
of
diketene
Diketene is an organic compound with the molecular formula , and which is sometimes written as . It is formed by dimerization of ketene, . Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry. It is a colorles ...
. Some derivatives, such as 3,3-dimethyl-oxetane-2,4-dione, are known.
[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. .]
References
{{Reflist
See also
*
Carbon suboxide
Carbon suboxide, or tricarbon dioxide, is an organic, oxygen-containing chemical compound with formula and structure . Its four cumulative double bonds make it a cumulene. It is one of the stable members of the series of linear oxocarbons , w ...
(C
3O
2), an anhydride of malonic anhydride.
* 2-oxetanone, also called
β-propiolactone
*
3-oxetanone
Carboxylic anhydrides
Oxetanes
Substances discovered in the 1980s