The new energetic materials 2-amino-5-nitrotetrazole (ANT, 1), 1-amino-3, 4-dinitro-1, 2, 4- triazole (ADNT, 2), and both 1, 1′-diamino-5, 5′-bistetrazole and 1, 2′-diamino-5, 5′- bistetrazole (11DABT, 3 and 12DABT, 4) have been prepared by the amination of the parent anion with O-tosylhydroxylamine. The 5-H-tetrazolate anion has also been aminated using hydroxylamine O-sulfonic acid to both 1-aminotetrazole and 2-aminotetrazole (1AT, 5 and ...