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Reductive Activation of Arenes: XIV. Effect of Medium on the Products Ratio in the Alkylation of Nitrobenzene Radical Anion Sodium Salt

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Abstract

The product of nitrobenzene reduction by 1 equiv of sodium reacted with tert-butyl iodide in liquid ammonia and its mixtures with tetrahydrofuran and hexamethylphosphoramide to afford a mixture of compounds alkylated either by the functional group (N-alkylation) or at the benzene ring (C-alkylation). The ratio of N- and C-alkylation products decreases in the solvents series NH3-THF (5.7) > NH3 (1.0) > NH3-HMPA (0.6).

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  1. Siberian Division, Russian Academy of Sciences, Vorozhtsov Novosibirsk Institute of Organic Chemistry, Novosibirsk, 630090, Russia

    B. A. Selivanov & V. D. Shteingarts

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  1. B. A. Selivanov
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  2. V. D. Shteingarts
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Selivanov, B.A., Shteingarts, V.D. Reductive Activation of Arenes: XIV. Effect of Medium on the Products Ratio in the Alkylation of Nitrobenzene Radical Anion Sodium Salt. Russian Journal of Organic Chemistry 37, 1719–1722 (2001). https://doi.org/10.1023/A:1013969901048

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