Illustrated Glossary of Organic Chemistry

Oxidative cleavage: A reaction in which a carbon-carbon bond is cleaved, with simultaneous oxidation of the carbons that had formed the carbon-carbon bond.

Alkyne ozonolysis is an oxidative cleavage reaction. For example, in the ozonolysis of phenylacetylene, the carbon-carbon triple bond is cleaved, and each carbon of this bond is oxidized to a carboxylic acid.


Treatment of an alkene with osmium tetroxide (OsO₄) and sodium periodate (NaIO₄) is an oxidative cleavage reaction. For example, treatment of methylcyclohexene with OsO₄ and NaIO₄ cleaves the carbon-carbon double bond. One carbon atom of the alkene bond is oxidized to an aldehyde and the other to a ketone.