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

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

研究成果: 雜誌貢獻文章

3 引文 (Scopus)

摘要

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.

原文英語
頁(從 - 到)153-161
頁數9
期刊Advanced Synthesis and Catalysis
342
發行號2
出版狀態已發佈 - 2000

指紋

Radiation counters
Dimerization
Anthracene
Dimers
Anions
Hydrogen
Negative ions
Electrons
anthracene

ASJC Scopus subject areas

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

引用此文

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.

Neglected Aspects of Anthracenide (Anthracenidyl) Chemistry -Reactions with two N-Benzoylaziridines. / Lin, Pen Yuan; Weiß, Rainer; Werry, Jürgen; Falkenstein, Reinhard; Stamm, Helmut.

於: Advanced Synthesis and Catalysis, 卷 342, 編號 2, 2000, p. 153-161.

研究成果: 雜誌貢獻文章

Lin, PY, Weiß, R, Werry, J, Falkenstein, R & Stamm, H 2000, 'Neglected Aspects of Anthracenide (Anthracenidyl) Chemistry -Reactions with two N-Benzoylaziridines', Advanced Synthesis and Catalysis, 卷 342, 編號 2, 頁 153-161.
Lin, Pen Yuan ; Weiß, Rainer ; Werry, Jürgen ; Falkenstein, Reinhard ; Stamm, Helmut. / Neglected Aspects of Anthracenide (Anthracenidyl) Chemistry -Reactions with two N-Benzoylaziridines. 於: Advanced Synthesis and Catalysis. 2000 ; 卷 342, 編號 2. 頁 153-161.
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AU - Stamm, Helmut

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N2 - 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.

AB - 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.

KW - Aziridines

KW - Dimerizations

KW - Electron transfer

KW - Heterocycles

KW - Radical ions

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