Oxidation of some sulfurand nitrogen-containing alkylphenols with hydroperoxides

Studied the oxidative conversion of 2,6-di-tert-butyl-4-propyl(ethylthiopropyl)phenols with some para-substituent (isothiuronium and alkylamine group) by hydrogen hydroperoxide and cumene hydroperoxide. It is shown that the trialkylamine and isothiuronium groups increases resistance to oxidative effect of peroxides. Heating of chloride S-(2-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propylthio) ethyl)isothiuronium and N,N-dimethyl-2-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propylthio)ethylamine with hydroperoxides were carried out corresponding sulfinyl derivatives. However, the oxidation N,N-dimethy-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propylamine under similar conditions resulted in virtually quantitative yield to the corresponding N-oxide. Meanwhile chloride S-(3-(3,5-di-tert-butyl-4-hydroxyphenyl) propyl)isothiuronium was resistant to the action of hydroperoxides to acidic and neutral media, but in the presence of alkali was oxidized to bis-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl)disulfide. All of the oxidation products isolated in pure form and characterized by spectral methods.