Synthesis and reactions of quinolide peroxides under acid-catalysis conditions

Abstract

1. The isomeric composition and structure of quinolide peroxides, formed in the oxidation of 4-R1-2,6-di-tert-butylphenols, are determined by steric and electronic effects of substituent R1. 2. By the action of acids, the quinolide peroxide derivatives of 4-R1-2,6-di-tert-butylphenols convert selectively in high yields into 2,6-di-tert-butyl-1,4-benzoquinone and 2,6-di-tert-butylhydroquinone. The rates of the reaction depend on the nature of substituent R1 and on the acidity of the medium. 3. The mechanism of conversion of the quinolide peroxides derived from 4-R1-2,6-di-tert-butylphenols in the presence of acids has been proposed and confirmed.