A theoretical study of the Duff reaction : insights into its selectivity
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Date
2016-10-07
Journal Title
Journal ISSN
Volume Title
Publisher
Royal Society of Chemistry
Abstract
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.
Keywords
Duff Reaction, Ortho-formylation of Phenols, DFT Calculations, Hydrogen Bond, Non-symmetrically Substituted Phenols