Designing the First Hydroxylamine Substituted Tetrazole With N , O‐ Dimethylhydroxylamine

Abstract

Nitrogen‐rich heterocyclic compounds, particularly 5‐substituted tetrazoles, are of significant importance in many fields such as energetic materials, pharmaceuticals, coordination chemistry and catalysis, and agrochemistry. Despite the extensive history of exploration of the tetrazole ring, the synthesis and isolation of 5‐hydroxylamine substituted tetrazoles have remained extremely elusive in literature, representing a notable gap in fundamental heterocyclic chemistry. This work represents the first successful synthesis and characterization of a 5‐hydroxylamine‐substituted tetrazole: 5‐( N , O ‐dimethylhydroxylamine)‐1 H ‐tetrazole and its hydrochloride salt.