An investigation of the products from the reaction of ozone with aminodinitrotoluenes (ADNTs) provides information about the oxidation pathway. Studies conducted at low conversions of 2- and 4-ADNT show 2:1 ozone/ADNT stoichiometries, prompt formation of glyoxylic and pyruvic acids, and NO2- and NO3- (NO,) ions. Reaction schemes to account for these results involve a 1,3-dipolar cycloaddition of ozone to selected double bonds of the aromatic ring, leading to ring cleavage. N-15-Labeling experiments indicate that the amino function is not involved in the initial ozone oxidation acid eventually is incorporated into pyruvamide (2-ADNT) and oxamic acid (4-ADNT) before being oxidized to nitrate. References: 20
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