Quantitative investigation of the ozonolysis reaction. IX. On the mechanism of ozonide formation

The ozonide cis-trans ratios, for both normal and cross-ozonides, have been examined, in a number of cases, in pentane and in benzene solutions. In benzene, at 25 °C, almost invariant cis-trans ratios are observed, regardless of the geometry and initial concentration of olefin. In pentane, these rat...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 47; no. 21; pp. 3921 - 3929
Main Authors Fliszár, Sándor, Carles, Jacques
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.11.1969
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Summary:The ozonide cis-trans ratios, for both normal and cross-ozonides, have been examined, in a number of cases, in pentane and in benzene solutions. In benzene, at 25 °C, almost invariant cis-trans ratios are observed, regardless of the geometry and initial concentration of olefin. In pentane, these ratios have been found to depend, both at −78 and 25 °C, on the geometry and the initial concentration of the olefin when 1,2-disubstituted ethylenes with bulky substituents are ozonized. However, the cross-ozonide cis-trans ratios obtained from trisubstituted ethylenes do not depend on the initial olefin concentration. A tentative mechanistic proposal is suggested in terms of transitory zwitterion-olefin adducts.
ISSN:0008-4042
1480-3291
DOI:10.1139/v69-654