Cyclobutanetetrone
Encyclopedia
Cyclobutanetetrone, also called tetraoxocyclobutane, is a hypothetical organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with formula C4O4 or (-(C=O)-)4, the fourfold ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

 of cyclobutane
Cyclobutane
Cyclobutane is an organic compound with the formula 4. Cyclobutane is a colourless gas and commercially available as a liquefied gas. Derivatives of cyclobutane are called cyclobutanes...

. It would be an oxide of carbon
Oxocarbon
An oxocarbon or oxide of carbon is an inorganic compound consisting only of carbon and oxygen.The simplest and most common oxocarbons are carbon monoxide and carbon dioxide...

, indeed a tetramer
Polymer
A polymer is a large molecule composed of repeating structural units. These subunits are typically connected by covalent chemical bonds...

 of carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...

.

The compound seems to be thermodynamically unstable. As of 2000, it had yet to be synthesized in significant amounts but may have transient existence as detected by mass spectrometry
Mass spectrometry
Mass spectrometry is an analytical technique that measures the mass-to-charge ratio of charged particles.It is used for determining masses of particles, for determining the elemental composition of a sample or molecule, and for elucidating the chemical structures of molecules, such as peptides and...

.

Related compounds

Cyclobutanetetrone can be viewed as the neutral counterpart of the squarate
Squaric acid
Squaric acid, also called quadratic acid, because its four carbon atoms approximately form a square, is an organic compound with chemical formula 424....

 anion C4O42−, which is stable and has been known at least since 1959.

The compound octahydroxycyclobutane or cyclobutane-1,1,2,2,3,3,4,4-octaol (-C(OH)2-)4 may be referred to in the literature as "hydrated tetraoxocyclobutane".
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