Abstract
Abstract1,3‐Dinitrobenzene (1a) and some simple monosubstituted derivatives (1b–g) were aminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to give the corresponding mono‐ and bis(methylamino)‐substituted compounds (3a‐e and 4a). 1,2‐Dinitrobenzene (1i) was aminated with LMA/PP to give 2‐(methylamino)‐1‐nitrobenzene (3f) in high yield. The intermediacy of 4‐(methylamino) σ‐adducts of 1,3‐dinitrobenzene (2a), 2‐chloro‐ (2b) and 2‐amino‐1,3‐dinitrobenzene (2c) was established by 1H‐NMR spectroscopy. Quantum‐chemical calculations for the dinitrobenzenes suggest that, in general, the experimentally observed regioselectivity of the methylamination is satisfactorily described by frontier molecular orbital (FMO) interaction of the reagents.
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