Journal of Organic Chemistry p. 115 - 121 (1989)
Update date:2022-08-24
Topics:
Wojciechowski, Brenda J.
Pearson, William H.
Kuczkowski, Robert L.
The ozonolysis of (E)-1-ethoxypropene (or (Z)-1-ethoxypropene) gave cis and trans pairs of 1,2-dioxolanes, 1,2,4-trioxolanes (ozonides), and 1,2,4,5-tetroxanes.Ozonolysis of mixtures of the E and Z alkenes led to variation in the dioxolane stereoisomer ratios but not in the trioxolane ratios.Ozonolysis in the presence of added alcohol or aldehydes produced hydroperoxides or ozonides, respectively, from the methyl-substituted carbonyl oxide.The results are consistent with a Criegee ozonolysis mechanism if the two alkenes produce different relative amounts of the syn and anti carbonyl oxide (CH3HCOO), which recombine at different rates with dipolarophiles.
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