- Amination of some 1,3-dinitrobenzenes with liquid ammonia-potassium permanganate
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1,3-Dinitrobenzene and some its 2- and 4-substituted derivatives are dehydroaminated in a solution of potassium permanganate in liquid ammonia to give the corresponding mono- or diamino-1,3-dinitro-benzenes. Under the same conditions, 4-fluoro-1,3-dinitrobenzene is converted into 2,4-dinitroaniline via replacement of the fluorine atom, while 2,4-dinitrobenzaldehyde gives rise to 2,4-dinitrobenzamide.
- Szpakiewicz,Grzegozek
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p. 829 - 833
(2007/10/03)
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- Amination of dinitrobenzenes with liquid methylamine/potassium permanganate
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1,3-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) ?-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.
- Wozniak, Marian,Grzegozek, Maria,Roszkiewicz, Witold,Szpakiewicz, Barbara
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