Malonic anhydride or oxetane-2,4-dione is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with
chemical formula
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 symbols, such as pare ...
C
3H
2O
3 or CH
2(CO)
2O. It can be viewed as the
anhydride
An acid anhydride is a type of chemical compound derived by the removal of water molecules from an acid (chemistry), acid.
In organic chemistry, organic acid anhydrides contain the functional group . Organic acid anhydrides often form when one ...
of
malonic acid
Malonic 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's diethyl ester. The name originates from ...
, or a double
ketone
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
of
oxetane.
Malonic anhydride was first synthesized in 1988 by
ozonolysis
In organic chemistry, ozonolysis is an organic reaction where the Saturated and unsaturated compounds, unsaturated bonds are Bond cleavage, cleaved with ozone (). Multiple carbon–carbon bond are replaced by carbonyl () groups, such as aldehydes ...
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 colorle ...
. 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. {{doi, 10.1021/jo01297a044.]
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 , wh ...
(C
3O
2), an anhydride of malonic anhydride.
* 2-oxetanone, also called
β-propiolactone
*
3-oxetanone
References
Carboxylic anhydrides
Oxetanes
Substances discovered in the 1980s