Synthesis and Properties of 1-Acyl Triazenes

Organic Letters
Iris R LandmanKay Severin

Abstract

1-Acyl triazenes can be prepared by acid-catalyzed hydration, gold/iodine-catalyzed oxidation, or oxyhalogenation of 1-alkynyl triazenes. Crystallographic analyses reveal a pronounced effect of the acyl group on the electronic structure of the triazene function. 1-Acyl triazenes display high thermal stability, and only moderate sensitivity toward hydrolysis. They are compatible with basic and oxidative conditions, allowing subsequent transformation. Under acidic conditions, 1-acyl triazenes act as acylation reagents.

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