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Updated: Dec 30, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Divergent Mechanisms of the Banert Cascade with Propargyl Azides
Juliana R Alexander1, Mary H Packard1, Alanna M Hildebrandt1
1Department of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, United States.
Abstract:
Triazoles are privileged heterocycles for a variety of applications. The synthesis of 1H-triazoles can be accomplished by the Banert cascade from propargylic azides. Depending on the substrate and conditions, the Banert cascade can proceed by either a sigmatropic or prototropic mechanism. This report describes the first detailed kinetic analysis of the Banert cascade proceeding by both pathways including substituent effects and KIE. The analysis identified the inflection point in the divergent pathways, allowing future work to predict which Banert products are accessible.
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