Tropolone

Tropolone is an organic compound with the chemical formula C7H6O2. It is a seven-membered aromatic ring and is notable for its uncommon 7-membered ring structure. Tropolone was first isolated in 1935 by the German chemist Walter Reppe and his colleagues, who produced it from cresol and carbon monoxide in a process now known as Reppe chemistry.

Structure and properties

Tropolone consists of a seven-membered ring with alternating single and double bonds, similar to the structure of benzene. However, unlike benzene, tropolone has a ketone functional group at one of its positions. This ketone group is in a state of continuous tautomerism with a nearby hydroxyl group, resulting in a structure that is best represented as a resonance hybrid of two forms.

Tropolone is a pale yellow solid that is soluble in water, alcohol, and ether. It has a characteristic strong odor and a bitter taste.

Synthesis

Tropolone can be synthesized from cresol and carbon monoxide in a process known as Reppe chemistry. This process involves the carbonylation of cresol to give a lactone, which is then rearranged to give tropolone.

Uses

Tropolone is used as a chelating agent in the synthesis of metal complexes. It is also used as a ligand in organometallic chemistry. In addition, tropolone has been studied for its potential use in organic electronics due to its ability to accept and donate electrons.

Safety

Tropolone is considered to be a mild irritant. It can cause irritation to the skin, eyes, and respiratory tract if inhaled or contacted.

See also

• Hydroxytropolone
• Tropolone (data page)

References

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