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

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 stag...

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Detalles Bibliográficos
Autores principales: Grimblat, Nicolás, Sarotti, Ariel Marcelo, Kaufman, Teodoro Saúl, Simonetti, Sebastián Osvaldo
Formato: article artículo publishedVersion
Lenguaje:Inglés
Publicado: Royal Society of Chemistry 2018
Materias:
Duff Reaction
Ortho-formylation of Phenols
DFT Calculations
Hydrogen Bond
Non-symmetrically Substituted Phenols
Acceso en línea:http://hdl.handle.net/2133/10491
http://hdl.handle.net/2133/10491
Aporte de:
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario
id I15-R121-2133-10491
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
orig_language_str_mv eng
topic Duff Reaction
Ortho-formylation of Phenols
DFT Calculations
Hydrogen Bond
Non-symmetrically Substituted Phenols
spellingShingle Duff Reaction
Ortho-formylation of Phenols
DFT Calculations
Hydrogen Bond
Non-symmetrically Substituted Phenols
Grimblat, Nicolás
Sarotti, Ariel Marcelo
Kaufman, Teodoro Saúl
Simonetti, Sebastián Osvaldo
A theoretical study of the Duff reaction : insights into its selectivity
topic_facet Duff Reaction
Ortho-formylation of Phenols
DFT Calculations
Hydrogen Bond
Non-symmetrically Substituted Phenols
description 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.
format article
artículo
publishedVersion
author Grimblat, Nicolás
Sarotti, Ariel Marcelo
Kaufman, Teodoro Saúl
Simonetti, Sebastián Osvaldo
author_facet Grimblat, Nicolás
Sarotti, Ariel Marcelo
Kaufman, Teodoro Saúl
Simonetti, Sebastián Osvaldo
author_sort Grimblat, Nicolás
title A theoretical study of the Duff reaction : insights into its selectivity
title_short A theoretical study of the Duff reaction : insights into its selectivity
title_full A theoretical study of the Duff reaction : insights into its selectivity
title_fullStr A theoretical study of the Duff reaction : insights into its selectivity
title_full_unstemmed A theoretical study of the Duff reaction : insights into its selectivity
title_sort theoretical study of the duff reaction : insights into its selectivity
publisher Royal Society of Chemistry
publishDate 2018
url http://hdl.handle.net/2133/10491
http://hdl.handle.net/2133/10491
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AT simonettisebastianosvaldo theoreticalstudyoftheduffreactioninsightsintoitsselectivity
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