Artículo

A theoretical study of the Duff reaction: Insights into its selectivity

Grimblat, NicolasIcon ; Sarotti, Ariel MarceloIcon ; Kaufman, Teodoro SaulIcon ; Simonetti, Sebastián OsvaldoIcon
Fecha de publicación: 10/2016
Editorial: Royal Society of Chemistry
Revista: Organic & Biomolecular Chemistry
ISSN: 1477-0520
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:

Resumen

The Duff reaction is one of the most employed methods for the ortho-formylation of phenols; however, not much is truly known about its mechanism. Using DFT calculations, we disclose the first theoretical study regarding the selectivity-determining step of the reaction. We have found that this stage is governed by a hydrogen bond, that gives rise to a cyclohexa-2,4-dienone intermediate and establishes the position where the formylation will take place. These findings were evaluated by analysis of the reaction outcome of several non-symmetrically substituted phenols.
Palabras clave: Duff Formylation , Theoretical Study , Selectivity , Hydrogen Bond
 
Archivos asociados
Thumbnail
 
Tamaño: 1.579Mb
Formato: PDF
.
Licencia
info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution 2.5 Unported (CC BY 2.5)
Identificadores
URI: http://hdl.handle.net/11336/52821
DOI: http://dx.doi.org/10.1039/C6OB01887D
URL: https://pubs.rsc.org/en/content/articlelanding/2016/ob/c6ob01887d#!divAbstract
Colecciones
Articulos(IQUIR)
Articulos de INST.DE QUIMICA ROSARIO
Citación
Grimblat, Nicolas; Sarotti, Ariel Marcelo; Kaufman, Teodoro Saul; Simonetti, Sebastián Osvaldo; A theoretical study of the Duff reaction: Insights into its selectivity; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 14; 44; 10-2016; 10496-10501
Compartir
Altmétricas