Synthesis and Spectroscopic Studies of Expanded Planar Dehydrotribenzo[n]annulenes Containing One or Two Isolated Alkene Units

W. Brad Wan, Ryan C. Chiechi, Timothy J.R. Weakley, Michael M. Haley

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Abstract

Dehydrobenzoannulene derivatives containing isolated alkene linkages were synthesized by combining an in-situ Pd/Cu-mediated cross-coupling with an intramolecular cyclization strategy. 1H NMR studies of these macrocycles and comparison with related systems verify that highly alkynylated dehydrobenzoannulenes possess weak induced ring currents, indicative of aromatic (4n+2 π-systems) and anti-aromatic (4n π-systems) behavior, in spite of their large size and extensive benzannulation.
Original languageEnglish
Pages (from-to)3485-3490
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2001
Issue number18
DOIs
Publication statusPublished - 2001

Keywords

  • Macrocycles
  • Cross-coupling
  • Aromaticity
  • Annulenes
  • Alkynes

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