Cyclobutanetetrone

Cyclobutanetetrone is a organic ketone that is characterized by its four carbon atoms arranged in a square planar structure, with each carbon atom double-bonded to an oxygen atom. It is a member of the cyclobutane family and is also known as squaric acid anhydride or squarone.

Structure and Properties

Structure of Cyclobutanetetrone

The structure of cyclobutanetetrone consists of a cyclobutane ring, where each carbon atom is double-bonded to an oxygen atom. This gives the molecule a square planar geometry. The molecular formula for cyclobutanetetrone is C₄O₄.

Cyclobutanetetrone is a highly reactive compound due to the strain in the four-membered ring and the presence of four carbonyl groups. It is also highly polar due to the presence of the oxygen atoms.

Synthesis

Cyclobutanetetrone can be synthesized from squaric acid by dehydration using acetic anhydride and sulfuric acid as catalyst. The reaction proceeds via the formation of an intermediate acyl chloride, which then undergoes intramolecular cyclization to form the cyclobutanetetrone.

Applications

Due to its high reactivity, cyclobutanetetrone is used as a building block in organic synthesis. It can undergo various reactions such as Diels-Alder reactions, Michael additions, and nucleophilic addition reactions, making it a versatile compound in the synthesis of complex organic molecules.

See Also

• Cyclobutane
• Ketone
• Organic synthesis
• Squaric acid