The p-toluenesulfonic acid-catalyzed reaction of ethyl diazoacetate with ethanol has been found to have different hydrogen isotope and solvent effects from the formally similar reaction with diphenyldiazomethane. Deuterium-exchange experiments have demonstrated that ethyl diazoacetate is involved in a rapid and reversible equilibrium with the corresponding diazonium ion with p-toluenesulfonic acid in ethanol, in the absence of strong acid in acetic acid or with acetic acid in benzene. It is concluded that the general-acid and “specific-oxonium” catalyzed reactions of diazo compounds involve different types of mechanisms.
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Roberts et al. (1952) studied this question.