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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:l 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 (p = -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.ROLAND J. TAILLEFER, SHIRLEY E. THOMAS, YVES NADEAU, S. FLISZAR et HERVE HENRY. Can. J. Chem. 58, 1138Chem. 58, (1980. Une etude systematique de la rtaction de I'ozone avec les acetals pour former les acktals hydrotrioxides A a t t t entreprise. On a trouve que la stoechiomttrie et I'ordre de la reaction etaient de un dans chacun des reactifs. L'effet des substituents sur la vitesse de reaction, mesure dans plusieurs systimes et sous difftrentes conditions de temperatures et de solvants est faible (p = -1.108 -1.58) de mime que I'effet de la polarit6 des solvants. Ces faits sont interpretis en invoquant un mecanisme d'addition 1,3-dipolaire de I'ozone dans le lien C-H de la fonction acetale.

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HERVB HENRY, SANDOR FLISZAR, and ANDRE JULG. Can. S. Chem. 54, 2085Chem. 54, (1976. An analysis of the molecular energy in terms of bond contributions indicates that the latter (eij) can be approximated by a linear combination of the changes in net charges qi and qj.