Collect. Czech. Chem. Commun. 1988, 53, 1033-1043

Formation of N-methyl-2-nitroso-4,6-dinitroaniline from methyl ester of N-methyl-N-(2,4,6-trinitrophenyl)glycine

Jaromír Kaváleka, Vladimír Macháčeka, Vojeslav Štěrbaa and Antonín Lyčkab

a Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice
b Research Institute of Organic Syntheses, 532 18 Pardubice-Rybitví


The reaction of methyl ester of N-methyl-N-(2,4,6-trinitrophenyl)glycine with methoxide in methanol produces N-methyl-2-nitroso-4,6-dinitroaniline. The kinetics of formation of the nitroso compound have been studied, and a mechanism of its formation has been suggested consisting in the intramolecular attack of CH2 group of aziridinone intermediate by oxygen atom of nitro group and in subsequent E2 elimination reaction. The aziridinone intermediate is formed by the attack of carbon atom of carboxylic group of 1,3-adduct of the starting ester with methoxide by the formally electroneutral tertiary nitrogen. In methoxide solution, N-methyl-2-nitroso-4,6-dinitroaniline undergoes another reduction-oxidation reaction giving 2-amino-2'-methylamino-3,3',5,5'-tetranitroazoxybenzene.