MICROWAVE SPECTRA OF OXYGEN-18 ETHYLENE AND PROPYLENE OZONIDE: OXYGEN-18 ALDEHYDE INSERTION OF THE OZONOLYSIS REACTION
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Publisher:Ohio State University
In the ozonolysis of mixtures of ethylene and oxygen-18 formaldehyde, at least 90\% of the aldehydic oxygen that incorporated in the ozonide ring was found at the epoxide site (JACS 94, 7609 (1972). In order to set a more precise upper limit for this incorporation and to ascertain if any oxygen-18 was incorporated at the peroxide site, the microwave spectra of several oxygen-18 sepecies of ethylene ozonide have been assigned. These species were prepared by ozonizing ethylene with oxygen-18 ozone. These assignments together with similar assignments for propylene ozonide were then used to determine the site of aldehydic oxygen incorporation. The reactions studied include the ozonolysis of: 1) ethylene and formaldehyde; 2) ethylene and acetaldehyde; 3) propylene and formaldehyde; 4) propylene and acetaldehyde; 5) 2-butene and formaldehyde. The results of this study are related to several mechanistic proposals for the ozonolysis reaction.
Author Institution: Department of Chemistry, University of Michigan
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