Tropolone

The compound has been of interest to research chemists because of its unusual electronic structure and its role as a ligand precursor.

[4] An alternate route is a [2+2] cycloaddition of cyclopentadiene with a ketene to give a bicyclo[3.2.0]heptyl structure, followed by hydrolysis and breakage of the fusion bond to give the single ring:[3] Thy hydroxyl group of tropolone is acidic, having a pKa of 7, which is in between that of phenol (10) and benzoic acid (4).

[4] The compound readily undergoes O-alkylation to give cycloheptatrienyl derivatives, which in turn are versatile synthetic intermediates.

There can be substantial hydrogen bonding between it and the hydroxyl group, leading to rapid tautomerization: the structure is symmetric on the NMR timescale.

[11] Tropolone arises via a polyketide pathway, which affords a phenolic intermediate that undergoes ring expansion.

Skeletal formula of tropolone
Skeletal formula of tropolone
Space-filling model of tropolone
Space-filling model of tropolone