Copper-catalysed oxidation of catechols by dioxygen

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Abstract

The catalytic activity of chloro(pyridine)copper(I) in the oxidation of 3,5-di-t-butylcatechol in dichloromethane and chloroform by dioxygen was studied kinetically. The reaction is quantitative and the overall rate equation shows second-order in the catalyst, first-order in the dioxygen and zero-order in the catechol concentrations, the rate-determining step being the formation of a dinuclear peroxo complex from the superoxo copper(I) species. The reaction can be used for the preparation of 3,5-di-t-butyl-o-benzoquinone. 4-t-Butylcatechol, 3,5-diisopropylcatechol, 9,10-dihydroxyphenanthrene and 3,5-dicyclohexylcatechol could be also oxidized to the corresponding quinones. No ring cleavage occurred as found with copper(I) chloride in pyridine solvent.

Original languageEnglish
Pages (from-to)259-267
Number of pages9
JournalJournal of molecular catalysis
Volume37
Issue number2-3
DOIs
Publication statusPublished - Oct 1986

ASJC Scopus subject areas

  • Engineering(all)

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