Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions

Robert J. Tombari, Jeremy R. Tuck, Noah Yardeny, Phillip W. Gingrich, Dean J. Tantillo, David E. Olson

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)7575-7580
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number35
DOIs
StatePublished - Sep 21 2021

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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