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Rates of hydroxide–ion induced cleavage of 2-diazo-1,3-indandione were measured in aqueous (H2O) sodium hydroxide solutions over the concentration range [NaOH] = 0.0004–0.1 M. The reaction was found to be first-order in hydroxide ion up to [NaOH] ≅ 0.01 M, but a second order term had to be added to account for the data in the region [NaOH] = 0.01–0.1 M. A mechanism is proposed involving hydroxide ion addition to one of the substrate carbonyl groups, and hydroxide–ion induced ionization of the O–H bond of this adduct in the more concentrated solutions, followed by C–C bond cleavage. Rates of acid–catalyzed transformation of the product of this cleavage, 2(diazoacetyl)benzoic acid, to 1,4-isochromandione were measured in aqueous (H2O and D2O) perchloric acid solutions over the concentration range [LClO4] = 0.0001–0.1 M and in formic acid and acetic acid buffers. The isotope effects that these data provide suggest that the reaction occurs by rate–determining proton transfer from hydronium ion to the substrate diazo carbon in the more acidic region of the range examined, but that in the less acidic region the reaction mechanism switches to intramolecular general acid catalysis by the substrate's carboxylic acid group.

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Kinetics and mechanism of the base–catalyzed cleavage of 2-diazo-1,3-indanedione and the acid–catalyzed decomposition of its hydrolysis product, 2-(diazoacetyl)benzoic acid