A Mechanism for Anomalous Ozonolysis

Following the ozonolysis of a series of allylic hydroxy olefins derived from manool (6) we propose a mechanism which accounts for the anomalous ozonolysis products of allylic hydroxyl compounds in nucleophilic and non- nucleophilic solvents. It involves intramolecular participation by the allylic hydroxyl to form a hydroperoxy epoxide rather than the 1,2- nucleophilic migration from carbon to oxygen as proposed in the Criegee rearrangement mechanism.