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...
Guardado en:
| Autores principales: | , , , |
|---|---|
| Formato: | article artículo publishedVersion |
| Lenguaje: | Inglés |
| Publicado: |
Royal Society of Chemistry
2018
|
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/2133/10491 http://hdl.handle.net/2133/10491 |
| Aporte de: |
| Sumario: | 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. |
|---|