Heterocyclic Nitrilimines and Their Use in the Synthesis of Complex High-Nitrogen Materials
Matthew L Gettings1,2,3, Sarah E Davis Finch4, Ashank Sethia5
1Department of Materials Engineering, Purdue University, 205 Gates Road, West Lafayette, Indiana 47906, United States.
Abstract:
We show the ability of a nitrilimine prepared from 3-amino-5-nitro-1,2,4-triazole to undergo various cyclization and rearrangement reactions, giving a beautiful diversity of nitrogen-rich heterocyclic products. This chemistry includes the first cyclization of a nitrilimine with a diazonium species, giving a tetrazole, a previously unknown transformation, as well as leading to the creation of several new energetic materials with backbones not available by traditional techniques. New materials prepared were characterized both chemically (multinuclear NMR, IR, mass spectrometry, and elemental analysis) and energetically, with sensitivities and performances reported.
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