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Ozonolysis of Alkenes

Ozonolysis of Alkenes Followed by Reduction: Introduction

Reaction principle

Ozonolysis is an important methodology for the cleavage of carbon-carbon double bonds. When used in preparative chemistry, the term ozonolysis includes several reaction steps. Introduction of ozone into a solution of an alkene generates a labile primary ozonide which rearranges to the more stable secondary ozonide. Subsequent reductive work-up with complete cleavage of the double bond yields two carbonyl derivatives, i.e. aldehydes, ketones or a mixture of both.

Example:

Fig.1

Application

In preparative chemistry, ozonolysis is only of limited importance. It is being used for the preparation of carbonyl compounds that are not available by other methods. However, the methodology is still valuable for the structure determination of natural products or elastomers.

Movie: Ozonolysis

Fig.
Ozonolysis of 1,10-diphenyl-decapentene
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