A systematic investigation of the reaction between ozone and acetals to form acetal hydrotrioxides A has been undertaken. The stoichiometry of the reaction has been shown to be 1:1 in each reactant and the order of the reaction was also one in each reactant. Substituent effects measured in a variety of systems and under several conditions of temperature and solvent were found to be small (ρ = −1.10 to −1.58). Solvent polarity was also found to have little effect on the rate of the reaction. Mechanistically, these facts are interpreted in terms of a 1,3-dipolar insertion of ozone into the C—H bond of the acetal function.
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Taillefer et al. (1980) studied this question.