The Absolute Best Science Experiment for 3-Hydroxyisobenzofuran-1(3H)-one

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The rate coefficients for the base-catalysed ring fission of a series of substituted benzocyclobutenediones to give the corresponding 2-formylbenzoic acids have been determined in water at 25.0 and 60.0C. The effects of 4-substituents and 4,5-di-substituents on the rates have been correlated using a modified Hammett equation to give a reaction constant, rho, equal to ca. 3.6 at 25.0C. The activation parameters have been calculated. The effect of solvent composition on the rates has been studied. The kinetic solvent isotope effect, product composition and enrichment in 18O-enriched water have also been studied. All the evidence indicates a mechanistic pathway which proceeds by rapid reversible addition of hydroxide anion to the dione, followed by intramolecular nucleophilic attack on the second carbonyl group and formation of a carbanionic intermediate.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1443O – PubChem