Novel illustrations of the specific reactivity of 1,1-diamino-2,2-dinitroethene (DADNE) leading to new unexpected compounds

1,1-Diamino-2,2-dinitroethene (DADNE) was further investigated and evaluated in oxidation and azidation reactions. DADNE gave new unexpected products as a result of its specific reactivity as previously observed. The X-ray structure determination was the key of success in this work enabling us to perfectly characterise the new products and argue about the reaction mechanisms as well. Once again, the nucleophilic gem-dinitrocarbon of DADNE seemed to be directly involved in these transformations. Attempts to change the regioselectivity were performed by modifying the experimental conditions.