Azido and Tetrazolo 1,2,4,5‐Tetrazine N‐Oxides

This study presents the synthesis and characterization of the oxidation products of 3,6‐diazido‐1,2,4,5‐tetrazine (1) and 6‐amino‐[1,5‐b]tetrazolo‐1,2,4,5‐tetrazine (2). 3,6‐Diazido‐1,2,4,5‐tetrazine‐1,4‐dioxide was produced from oxidation with peroxytrifluoroacetic acid, and more effectively using hypofluorous acid, and 2 can be oxidized to two different products, 6‐amino‐[1,5‐b]tetrazolo‐1,2,4,5‐tetrazine mono‐N‐oxide and di‐N‐oxide. These N‐oxide compounds display promising performance properties as energetic materials. The oxidation products of 3,6‐diazido‐1,2,4,5‐tetrazine (1) and 6‐amino‐[1,5‐b]tetrazolo‐1,2,4,5‐tetrazine (2) have been characterized. 3,6‐Diazido‐1,2,4,5‐tetrazine‐1,4‐dioxide (see picture) was produced by oxidation of 1 with peroxytrifluoroacetic acid, and more effectively using hypofluorous acid, and 2 can be oxidized to its mono‐ and di‐N‐oxide. These products display promising performance as energetic materials.