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Issue 44, 2016
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A theoretical study of the Duff reaction: insights into its selectivity

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Abstract

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.

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

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Publication details

The article was received on 26 Aug 2016, accepted on 07 Oct 2016 and first published on 07 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01887D
Citation: Org. Biomol. Chem., 2016,14, 10496-10501
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    A theoretical study of the Duff reaction: insights into its selectivity

    N. Grimblat, A. M. Sarotti, T. S. Kaufman and S. O. Simonetti, Org. Biomol. Chem., 2016, 14, 10496
    DOI: 10.1039/C6OB01887D

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