Novosibirsk State Pedagogical University Bulletin, 2015, vol. 5, no. 4, pp. 59–67
© Kandalintseva N. V., Prosenko O. I., Akhmetgareeva A. R., Yagunov S. E., Prosenko A. E., 2015
UDC: 
547-327 547.564

Oxidation of some Sulfur- and Nitrogen-Containing Alkylphenols with Hydroperoxides

Kandalintseva N. V. 1 (Novosibirsk, Russian Federation), Prosenko O. I. 1 (Novosibirsk, Russian Federation), Akhmetgareeva A. R. 1 (Novosibirsk , Russian Federation), Yagunov S. E. 1 (Novosibirsk, Russian Federation), Prosenko A. E. 1 (Novosibirsk, Russian Federation)
1 Novosibirsk State Pedagogical University, Novosibirsk, Russian Federation
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Abstract: 

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.

Keywords: 

aminoalkylphenols, thioalkylphenols, isothiuronium salts, N-oxides, sulfoxides, hydroperoxides

https://elibrary.ru/item.asp?id=23917475

For citation:
Kandalintseva N. V., Prosenko O. I., Akhmetgareeva A. R., Yagunov S. E., Prosenko A. E. Oxidation of some Sulfur- and Nitrogen-Containing Alkylphenols with Hydroperoxides. Novosibirsk State Pedagogical University Bulletin, 2015, vol. 5, no. 4, pp. 59–67. DOI: http://dx.doi.org/10.15293/2226-3365.1504.06
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Date of the publication 13.08.2015