Oxidation of aminodinitrotoluenes with ozone: Products and pathways

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