MECHANISM OF THE OZONOLYSIS OF PROPENE IN THE LIQUID PHASE.

Article abstract of DOI:10.1021/ja00352a030

Propylene was ozonized in isobutane, hlorodifluoromethane, and methyl chloride solvents. Propylene ozonide, ethylene ozonide, and 2-butene ozonide (cis and trans isomers) were obtained in ratios of about 82:16:2. The amount of butene ozonide increased while that of ethylene ozonide usually decreased for reactions in the presence of added acetaldehyde. The cis-trans stereochemistry of the butene cross ozonide from propylene was studied at various conditions. Usually the cis isomer was preferentially formed, but addition of acetaldehyde could alter this. The cis-(trans-butene ozonide ratio was 67/33 when formed from cis- or trans-2-butene in CHClF//2 and 50/50 as a cross ozonide from trans-2-pentene. The kinetic secondary isotope effects upon ozonolysis of propene-2-d//1 (k//H/k//D equals 0. 88 (6) and propene-1-d//1 (0. 88 (8) were evaluated. These results are discussed with reference to the Criege mechanism of ozonolysis. 37 refs.