Extending the haloform reaction to non-methyl ketones: Oxidative cleavage of cycloalkanones to dicarboxylic acids using sodium hypochlorite under phase transfer catalysis conditions

Cyclohexanone is readily oxidized to adipic, α,α-dichloroadipic, glutaric and succinic acids by sodium hypochlorite under phase transfer conditions. The selectivity is highly dependent on the pH of the reacting system. A consecutive chlorination-hydrolysis mechanism is proposed in which only cyclohexanone is a reactive substrate leading in parallel to the melange of oxidized products. Cyclooctanone and cyclopentanone are similarly oxidized.