Synthesis of N??alkoxybenzimidoyl azides and their reactions in electrophilic media

DD Dolliver, T Sommerfeld, ML Lanier…

Index: Dolliver, Debra D.; Sommerfeld, Thomas; Lanier, Megan L.; Dinser, Jordan A.; Rucker, Richard P.; Weber, Rebecca J.; McKim, Artie S. Journal of Physical Organic Chemistry, 2010 , vol. 23, # 3 p. 227 - 237

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Citation Number: 3

Abstract

Abstract A new general route to N-alkoxybenzimidoyl azides [ArC (N 3)= NOR] from a reaction of N-alkoxybenzimidoyl bromide [ArC (Br)= NOR] with sodium azide in DMSO is described. These reactions result in the Z-geometric configuration. These compounds show a moderate degree of thermal stability as assessed by differential scanning calorimetry, and lack reactivity in traditional 1, 3-dipolar cycloaddition 'click'reactions. Upon exposure to ...