Issue 35, 2021

Calculated oxidation potentials predict reactivity in Baeyer–Mills reactions

Abstract

Azobenzenes are widely used as dyes and photochromic compounds, with the Baeyer–Mills reaction serving as the most common method for their preparation. This transformation is often plagued by low yields due to the formation of undesired azoxybenzene. Here, we explore electronic effects dictating the formation of the azoxybenzene side-product. Using calculated oxidation potentials, we were able to predict reaction outcomes and improve reaction efficiency simply by modulating the oxidation potential of the arylamine component.

Graphical abstract: Calculated oxidation potentials predict reactivity in Baeyer–Mills reactions

Supplementary files

Article information

Article type
Communication
Submitted
24 Jul 2021
Accepted
17 Aug 2021
First published
17 Aug 2021

Org. Biomol. Chem., 2021,19, 7575-7580

Calculated oxidation potentials predict reactivity in Baeyer–Mills reactions

R. J. Tombari, J. R. Tuck, N. Yardeny, P. W. Gingrich, D. J. Tantillo and D. E. Olson, Org. Biomol. Chem., 2021, 19, 7575 DOI: 10.1039/D1OB01450A

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