Neglected Aspects of Anthracenide (Anthracenidyl) Chemistry -Reactions with two N-Benzoylaziridines

Pen Yuan Lin, Rainer Weiß, Jürgen Werry, Reinhard Falkenstein, Helmut Stamm

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Reaction of anthracenide A- with N-benzoylaziridines 1a,b forms charged radicals 3a,b by single electron transfer and homolytic ring opening. Reactions follow that are known or expected as e.g. coupling with position 9 of A.- forming dihydroanthracene anions 9a,b that yield amidoethylated dihydroanthracenes 10a,b, or react with 1a,b giving finally 9,10-bis-amidoethylated dihydroanthracenes 11a,b. Results depend on experimental conditions and on the counter ions Na+ or Li+. Coupling is not regiospecific: contributions by positions 2 and 1 reach 29% or 4%, respectively, of total coupling with the primary radical 3a; much higher contributions are possible with Li. Product 21s (probably 3,3′-disubstituted tetrahydrobianthryl) may arise by hydrogen detachment from the first intermediate (29) of coupling with position 2 and dimerization of the formed 2-substituted A.- (30). Coupling products may be fully aromatized or may be hydroxylated in one of the benzylic positions. With counter ion Li+ a non-SET reaction of 1a with the dimer of A.- is indicated by the isolation of 9-benzoyl-dihydroanthracene 15 and by 19% yield of 16a (aromatized 10a). Reaction of 3b with anthracene is indicated by 10,10′-disubstituted tetrahydrobianthryl 37.

Original languageEnglish
Pages (from-to)153-161
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume342
Issue number2
Publication statusPublished - 2000

Keywords

  • Aziridines
  • Dimerizations
  • Electron transfer
  • Heterocycles
  • Radical ions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Chemistry (miscellaneous)
  • Organic Chemistry

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  • Cite this

    Lin, P. Y., Weiß, R., Werry, J., Falkenstein, R., & Stamm, H. (2000). Neglected Aspects of Anthracenide (Anthracenidyl) Chemistry -Reactions with two N-Benzoylaziridines. Advanced Synthesis and Catalysis, 342(2), 153-161.