Electrophilic substitution of thetert-butyl-NNO-azoxy group by the bromine atom |
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Authors: | A E Frumkin A M Churakov V A Tartakovsky |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation |
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Abstract: | The electrophilic substitution of thetert-butyl-NNO-azoxy group by the bromine atom was observed for the first time when 6-bromo-2,4-bis(tert-butyl-NNO-azoxy)-5-chloro-1,3-phenylenediamine was treated with bromine in AcOH. The structural factors promoting this reaction are
discussed. The direction of the replacement was confirmed by PM3 calculations of the heats of formation of intermediate cationic
σ-adducts.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2131–2134, November, 1999. |
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Keywords: | meta-phenylenediamine derivatives azoxy compounds substitutive electrophilic bromination |
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