IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
A theoretical study of the Duff reaction: insights into its selectivity
Autor/es:
ARIEL M. SAROTTI; TEODORO S. KAUFMAN; NICOLÁS GRIMBLAT; SEBASTIÁN O. SIMONETTI
Revista:
ORGANIC & BIOMOLECULAR CHEMISTRY
Editorial:
ROYAL SOC CHEMISTRY
Referencias:
Lugar: CAMBRIDGE; Año: 2016 vol. 14 p. 10496 - 10501
ISSN:
1477-0520
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.
