Wagner−Meerwein Skeletal Rearrangement of 3-Spiroannulated 6,8a-Epoxy- and 6,8a;7,8-Diepoxyisoquinolines (3-Aza-11-oxatricyclo[6.2.1.01,6]undec-9-enes). Isolation and Identification of 5-Aza-2-oxatricyclo[6.2.1.03,9]undec-3-enes

Wagner−Meerwein Skeletal Rearrangement of 3-Spiroannulated 6,8a-Epoxy- and 6,8a;7,8-Diepoxyisoquinolines (3-Aza-11-oxatricyclo[6.2.1.01,6]undec-9-enes). Isolation and Identification of 5-Aza-2-oxatricyclo[6.2.1.03,9]undec-3-enes

The reactions of 3-acetyl-3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene and its 9,10-epoxy derivative with bromine and Ac2O/BF3·OEt2 under different conditions were studied. Unusual products of Wagner−Meerwein rearrangement bearing the olefin fragment (5-aza-2-oxatricyclo[6.2.1.03,9]undecen-3-enes) we...

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Veröffentlicht in:Journal of organic chemistry 2004-01, Vol.69 (2), p.432-438
Hauptverfasser: Zubkov, Fedor I, Nikitina, Eugenia V, Turchin, Konstantin F, Aleksandrov, Grigorii G, Safronova, Anastasia A, Borisov, Roman S, Varlamov, Alexey V
Format: Artikel
Sprache:eng
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Zusammenfassung:The reactions of 3-acetyl-3-aza-11-oxatricyclo[6.2.1.01,6]undec-9-ene and its 9,10-epoxy derivative with bromine and Ac2O/BF3·OEt2 under different conditions were studied. Unusual products of Wagner−Meerwein rearrangement bearing the olefin fragment (5-aza-2-oxatricyclo[6.2.1.03,9]undecen-3-enes) were isolated and characterized by X-ray analysis.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0353684