Oxyfunctionalization of Hydrocarbons. 3: Superacid Catalyzed Oxygenation of Alkanes with Ozone Involving Protonated Ozone, O3H+
Part 2: G. A. Olah, N. Yoneda, and D. G. Parker, J. Am. Chem. Soc., 98, 2251 (1976).
The reaction of ozone with a series of alkanes in superacid–SO2CIF solution has been investigated. Product analysis reveals that the reaction pathway involves oxygenation followed by a carbon to oxygen alkyl group migration analogous to the acid-catalyzed cleavage–rearrangement reaction of hydroperoxides. Mechanistic studies are consistent with electrophilic insertion into a σ bond by protonated ozone, O3H+.