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.