An investigation of the reaction between ozone and decalin

Abstract

The reaction of ozone with cis-- and trans-'decalin in the Liquid phase has been investigated. Neutral and acidic products have been identified and quantitatively estimated by gas+Li.quid chromatographic analysis s, The effects of temperature~ solvents and irradiation on product formation have been examined, and in addition changes caused by the presence of a typical autoxidation catalyst and inhibitor have been followed. Reaction has been carried out with various ozone concentrations and in the absence of oxygen. The major products obtained result from reaction at the bridgehead carbon=hydrogen bonds, and botn cis- and txcane-srdecalol are obtained from cis-decalin and from trans-decalin. A mechanistic scheme to account for the formation of both 9decalols f!~m trans-decalin il;!proposed which postulates the formation of a relatively stable tertiary hydrotrioxide intermediate which subsequently reacts with ozone by a radical process. The hydrotrwxide from cis-decalin, however, is regarded as unstable and.is assumed to collapse mainly to cis-9-'decalel before reaction with ozone occurs.