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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