Electrophilic amination and reactions with nitroarenes

Alkylmagnesium reagents react with 4-nitroanisole by different mechanisms, giving in THF at —70 °C a number of products. Oxidation by KMnOa in liquid NH3 affords, depending on the alkyl chain, mixtures of nitrosoanisol and 2-alkyl-4-nitroanisol.314 

The synthesis of 7-substituted indoles from ortfe-substituted nitroarenes and alkenylmagnesium halides is known as the Bartoli reaction.315 Usually, ortfe-unsubstituted nitroarenes give complex mixtures of products. In some cases 

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