Decomposition of Peroxybenzoic Acid in Solution. I. Decomposition in Alcohols

Decomposition of peroxybenzoic acid was studied in methyl, ethyl, isopropyl and tert-butyl alcohol. The primary and the secondary alcohols were oxidized to the corresponding carbonyl compounds, which were sometimes further oxidized. The apparent decomposition rate of peroxybenzoic acid in alcohols decreased in the order: isopropyl alcohol > ethyl alcohol > methyl alcohol >> tert-butyl alcohol. For these decompositions a radical mechanism, which involves the homolytic rupture of peroxybenzoic acid and its induced decomposition by 1-hydroxyalkyl radicals derived from the respective alcohols, was proposed. A possible participation of peroxybenzoate anions in these decompositions was suggested.