Kinetics of Ozonation. 6. Polycyclic Aliphatic Hydrocarbons.

Article abstract of DOI:10.1021/jo00250a005

The reaction of ozone with norbornane, adamantane and bicyclo<2.2.2>octane has been studied, including kinetics and product studies as well as the determination of activation paprameters for the ozonation of norbornane.This work was carried out to distinguish between hydride abstraction and a concerted insertion mechanism for the ozonation of C-H bonds.Kinetically, norbornane behaves like a secondary hydrocarbon and lacks the rate acceleration expected if a carbocation intermediate were involved in a hydride abstraction mechanism.We interpret this and other results as supporting a 1,3-dipolar insertion mechanism for the reaction of ozone with C-H bonds.