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Nitro group substitution in 2,4,6-trinitrotoluene under the action of arenethiols and transformations of the reaction products

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Abstract

The reactions of 2,4,6-trinitrotoluene with arenethiols in the presence of inorganic bases in dipolar aprotic solvents led to the replacement exclusively of the ortho-nitro group to form 2-arylthio-4,6-dinitrotoluenes. Substitution, oxidation, and reduction of the latter and their transformation products provided the basis for the preparation of mono- and di-ortho-S-substituted nitrotoluenes and aminotoluenes. Factors favoring the regiospecificity of ortho-substitution in 2,4,6-trinitrotoluene are discussed.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    O. V. Serushkina, M. D. Dutov, V. N. Solkan & S. A. Shevelev

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  1. O. V. Serushkina
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  2. M. D. Dutov
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  3. V. N. Solkan
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  4. S. A. Shevelev
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Serushkina, O.V., Dutov, M.D., Solkan, V.N. et al. Nitro group substitution in 2,4,6-trinitrotoluene under the action of arenethiols and transformations of the reaction products. Russian Chemical Bulletin 50, 2406–2410 (2001). https://doi.org/10.1023/A:1015095832081

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