Oxyfunctionalization of Hydrocarbons. 6: Electrophilic Oxygenation of Aliphatic Alcohols, Ketones, and Aldehydes with Ozone in Superacids. Preparation of Bifunctional Derivatives

The reaction of ozone with aliphatic alcohols, ketones, and aldehydes in magic acid–SO₂CIF or FSO₃H solution has been investigated. Experimental results indicate the reactions proceed via electrophilic insertion of protonated ozone into the C–H σ bonds of the substrates at positions γ- or further removed from the oxonium centers present in the superacidic media. No oxidation products of the protonated (and thus protected) carbinol or carbonyl groups were observed. The reactions allow the preparation of bifunctional oxygenated derivatives.