Experimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azides

[3,3]-Sigmatropic rearrangement of isoprenyl azides has been extensively investigated in an experimental and theoretical level. Prenylazides with different chain lengths and phenyl prenylazide have been synthesized. NMR analysis of each azide has been made to determine the equilibrium composition,...

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Autores principales: Porta, Exequiel Oscar Jesús, Vallejos, Margarita M., Bracca, Andrea Beatriz Juana, Labadie, Guillermo Roberto
Formato: article artículo publishedVersion
Lenguaje:Inglés
Publicado: Royal Society of Chemistry 2021
Materias:
Reacciones Pericíclicas
Reordenamiento Sigmatropico
Prenilazidas
Acceso en línea:http://hdl.handle.net/2133/19641
http://hdl.handle.net/2133/19641
Aporte de:
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario
id I15-R121-2133-19641
record_format dspace
institution Universidad Nacional de Rosario
institution_str I-15
repository_str R-121
collection Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR)
language Inglés
topic Reacciones Pericíclicas
Reordenamiento Sigmatropico
Prenilazidas
spellingShingle Reacciones Pericíclicas
Reordenamiento Sigmatropico
Prenilazidas
Porta, Exequiel Oscar Jesús
Vallejos, Margarita M.
Bracca, Andrea Beatriz Juana
Labadie, Guillermo Roberto
Experimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azides
topic_facet Reacciones Pericíclicas
Reordenamiento Sigmatropico
Prenilazidas
description [3,3]-Sigmatropic rearrangement of isoprenyl azides has been extensively investigated in an experimental and theoretical level. Prenylazides with different chain lengths and phenyl prenylazide have been synthesized. NMR analysis of each azide has been made to determine the equilibrium composition, showing the predominance of primary allyl azides over the tertiary ones and E over Z isomer, regardless of the chain length, temperature, solvent or the regiochemistry of the precursor isoprenyl alcohol. It was determined that phenyl prenylazides do not experience [3,3]-sigmatropic rearrangement. In order to rationalize the experimental results and to gain insight in the mechanism of the [3,3]-sigmatropic rearrangement of prenylazides a theoretical study was performed using density functional theory and the QTAIM approach.
format article
artículo
publishedVersion
author Porta, Exequiel Oscar Jesús
Vallejos, Margarita M.
Bracca, Andrea Beatriz Juana
Labadie, Guillermo Roberto
author_facet Porta, Exequiel Oscar Jesús
Vallejos, Margarita M.
Bracca, Andrea Beatriz Juana
Labadie, Guillermo Roberto
author_sort Porta, Exequiel Oscar Jesús
title Experimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azides
title_short Experimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azides
title_full Experimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azides
title_fullStr Experimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azides
title_full_unstemmed Experimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azides
title_sort experimental and theoretical studies of the [3,3]- sigmatropic rearrangement of prenyl azides
publisher Royal Society of Chemistry
publishDate 2021
url http://hdl.handle.net/2133/19641
http://hdl.handle.net/2133/19641
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