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Ozonolysis of Alkenes

Ozonolysis of Alkenes Followed by Reduction: Proof of Mechanism

The presence of the carbonyl oxide during ozonolysis can be confirmed by trapping the intermediate.


For example, the ozonolysis of ketene diethylacetal (1,1-diethoxyethylene) yields diethyl carbonate in addition to carbonyl oxide after cleavage of the primary ozonide . The carbonate only reacts very slowly with the carbonyl oxide because of its non-reactive, electron-rich character. The addition of a more reactive ketone, for example acetone, gives a mixed secondary ozonide. Using methanol as a solvent yields a hydroperoxide. In the absence of trapping reagents, the carbonyl oxide dimerizes to form the very explosive tetroxane.

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