1-Alkynyltriazenes as Functional Analogues of Ynamides

The chemical reactivity of 1‐alkynyltriazenes has been investigated and is found to parallel the reactivity of ynamides. The similarity in reactivity of these two classes of compounds is demonstrated by addition reactions with acids, by cycloaddition reactions with ketenes, tetracyanoethene, and cyclopropanes, as well as by intramolecular cyclization reactions. The presence of reactive triazene groups in the products enables subsequent transformations. Overall, our results suggest that 1‐alkynyltriazenes should become valuable reagents in synthetic organic chemistry. Aus gleichem Holz geschnitzt: 1‐Alkinyltriazene sind aktivierte Alkine mit einem ähnlichen Reaktivitätsprofil wie Inamide. Die Reaktivitäten beider Verbindungsklassen werden in einer Serie verschiedener Reaktionen verglichen. Die in den Produkten vorhandene Triazengruppe erleichtert Folgereaktionen.