Ozonolysis of verbenone in aprotic solvents

The ozonolysis of verbenone in methylene chloride and acetonitrile at –60 and 0 °C proceeds with cleavage of the double bond and neighbouring σ-bond to give (1 R ,3 S )-acetyl-2,2-dimethylcyclobutane carboxylic acid. The mechanism of the reaction has been proposed.