As you might guess, organic ozonides are derived from ozone. So let’s first consider the nature of ozone. The ozone molecule is bent and unstable. It is thus polarized and quick to react with unsaturated molecules, notably alkenes. The image illustrates the result. What, however, is the mechanism producing the result in a typical case?¹
Initially, all three oxygen molecules add to the alkene on the same side of what was previously a double bond. This structure, however, is a transient intermediate, which rearranges to form the ozonide structure. Ozonides are relatively stable. However, they can be readily split to yield a pair of carbonyl compounds.
Organic Ozonides in Synthesis
Some ozonides are explosive, so they are seldom isolated. However, ozonides can be made to undergo a number of useful synthetic reactions. A few of these are illustrated in our third image.
Note: You might also enjoy Ozone – the Other Oxygen
¹The organic chemist all too often experiences factors that alter a “typical case”.
Note: You might also enjoy Forming Nitrogen Heterocycles from Aliphatic Amino Acids https://www.quirkyscience.com/nitrogen-heterocycles/
- Yale University: Ozonolysis
- Wiley: Angewandte Chemie: Mechanism of Ozonolysis by R. Criegee
- Advanced Organic Chemistry, 4th Ed. by Jerry March – John Wiley & Sons