Divergent Mechanisms of the Banert Cascade with Propargyl Azides

Autor:	Mary H. Packard, Joseph J. Topczewski, Juliana R. Alexander, Alanna M. Hildebrandt, Amy A. Ott
Rok vydání:	2020
Předmět:	Azides 010405 organic chemistry Organic Chemistry Kinetic analysis Substituent Triazoles Sigmatropic reaction 010402 general chemistry 01 natural sciences Article 0104 chemical sciences Kinetics chemistry.chemical_compound Banert cascade chemistry Computational chemistry Propargyl
Zdroj:	J Org Chem
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.9b03061
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::92402316c5504cbc786fb31ca54177f4 https://doi.org/10.1021/acs.joc.9b03061 Zobrazit plný text záznamu