Nucleophilic Attack of Azide at Electrophilic Azides: Formation of N₆ Units in Hexazene and Aminopentazole Derivatives

Abstract

N labeling experiments, it has been confirmed that nucleophilic attack of azide at iminium-activated organic azides leads to short-lived hexazene intermediates. Such species do not only tend to a cleavage reaction with formation of N-azido compounds, but also undergo ring closure to generate unprecedented amidino-functionalized pentazoles. Thus, treatment of the parent Vilsmeier reagent with two equivalents of sodium azide creates an aminopentazole derivative as the main product, which is easily characterized by NMR spectroscopy.

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