Formation of 4,6-dinitro-2-nitrosoaniline by intramolecular redox reaction of esters and amides of 2-(2,4,6-trinitroaniline) carboxylic acids

Abstract

The reaction of methyl and ethyl esters of N-(2,4,6-trinitrophenyl) glycine and N-(2,4,6-Trinitrophenyl)α-alanine (3a–d) with methoxide ion in methanol produces 4,6-dinitro-2-nitrosoaniline (4). N-(2,4,6-Trinitrophenyl) glycine methylamide (1d) gives, under the same conditions, the nitroso compound (4) in addition to 12% of the spiro adduct (2d). A reaction mechanism is suggested, and the influence of the side chain on the reaction kinetics has been studied.