N,N′-dimethyl-N,N′-diarylurea anion radicals: An intramolecular reductive elimination

Todd L. Kurth, Frederick D. Lewis, Chris M. Hattan, Richard C. Reiter, Cheryl D. Stevenson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations


The one-electron reduction of tertiary N,N′-dimethyl-N,N′-diarylureas (aryl = phenyl, β-naphthyl, α-naphthyl), in HMPA, results in anion radicals that undergo novel intramolecular reductive elimination reactions leading to the formation of the anion radicals of the corresponding biaryls. These results are due to face to face π-π stacking interactions involving the two aromatic rings in the urea systems. The overlapping pπ orbitals on the ipso carbons of opposing aryl groups evolve into a σ bond leading to the formation of the biaryl anion radical. In the case of the N,N′-dimethyl-N,N′-di-2-pyrenylurea system, there is a node in the LUMO of the number 2 carbon, and the parent anion radical remains intact.

Original languageEnglish (US)
Pages (from-to)1460-1461
Number of pages2
JournalJournal of the American Chemical Society
Issue number6
StatePublished - Feb 12 2003

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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