Abstract
in theinitial steps to give the primary ozonides 2 and theinitial fragments 3 and 4, the latter do undergo[3+2]-cycloaddition to give ozonide 5. Hence, thecarbonyl oxide fragments 3 undergo side reactionswhich often lead to peroxidic materals other thanozonides, particularly acyclic and cyclic oligomersof 3, such as dimers of structure 6 and polymers ofstructure 7. Neverthless, this method failed when applied to avariety of substrates such as most tetrasubstitutedethylenes, monocyclic olefins except for those hav-ing four to six-membered rings, certain bicyclic ole-fins, certain acyclic conjugated dienes, cyclicpolyenes, and aromatic compounds. The failure ofthese substrates to afford the corresponding ozo-nides have been attributed to the low reactivity ofensuing ketone fragments 4 in 1,3-dipolar cycload-dition. However, it was very recently that Gries-baum et al. have been able to prepare the ozonidesof larger cyclic olefins and bicyclic olefins by appli-cation of the modified ozonolysis on polyethylene.
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