Thermally Driven Tetrazine-to-Triazole Ring Contraction Mediated by Hydroxylammonium Cations

Key Points

• This research aims to explore the reactivity of nitroimine-functionalized tetrazine with various cations, particularly hydroxylamine.
• Examined cation-dependent reactions involving ammonia, hydrazine, and hydroxylamine with nitroimine-functionalized tetrazine.
• Analyzed the thermal transformation of tetrazine to triazole induced by hydroxylammonium cations.
• Hydroxylamine induces a thermally driven conversion from tetrazine to triazole.
• Stable salts are formed with ammonia and hydrazine, showcasing distinct reaction pathways.