Mechanism of Ozonolysis. The Initial Ozonide. Lack of Evidence for "Unified Concept" Involving Staudinger Molozonide

Abstract

Contrary to previous reports cyclohexanone and pinacolone are not oxidized to the corresponding Baeyer–Villiger oxidation products during ozonolysis of ethylidenecyclohexane in their presence. Addition of propionaldehyde to a solution of the 1,2,3-trioxolane initial ozonide of trans-1,2-di-t-butylethylene resulted in oxidation of the aldehyde to propionic acid and reduction of the 1,2,3-trioxolane to pivaldehyde. Thus, there is no necessity for the four-membered Staudinger molozonide as an ozonolysis intermediate, as recently proposed by Story.