A push-pull azobenzene is mercurated twice at the ring with less electron density

Philip J.W. Elder, Jeff C. Landry, Anthony F. Cozzolino, Allison E.A. Chapman, Ignacio Vargas-Baca

Research output: Contribution to journalArticle

Abstract

Treatment of N,N-dialkyl-4-[4-nitrophenyl)diazenyl] anilines with a mercury(II) salt in anhydrous trifluoroacetic acid results in single and double metallation of the ring with less electron density. The seemingly counterintuitive outcome of the reaction was rationalized through experimental and computational investigations of the reaction mechanism.

Original languageEnglish
Pages (from-to)11-18
Number of pages8
JournalJournal of Organometallic Chemistry
Volume716
DOIs
StatePublished - Oct 1 2012

Keywords

  • Azodyes
  • DFT calculations
  • Electrophilic substitution
  • Functionalization of azobenzenes
  • Mercuration
  • Metallation reactions

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