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Wagner-Meerwein Skeletal Rearrangement of 3-Spiroannulated 6,8a-Epoxy- and 6,8a;7,8-Diepoxyisoquinolines (3-Aza-11-oxatricyclo[ 1,6]undec-9-enes). Isolation and Identification of 5-Aza-2-oxatricyclo[,9]undec-3-enes

By Zubkov F.I., Nikitina E.V., Turchin K.F., Aleksandrov G.G., Safronova A.A., Borisov R.S. and Varlamov A.V.


The reactions of 3-acetyl-3-aza-11-oxatricyclo[ 1,6]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[ 3,9]-undecen-3-enes) were isolated and characterized by X-ray analysis

Topics: Bromine, Derivatives, Olefins, Reaction kinetics, X ray analysis, Olefin fragments, Aromatic compounds, 5 aza 2 oxatricyclo[ 3,9]undec 3 ene, 6,8a epoxyisoquinoline (3 aza 11 oxatricyclo[ 1,6]undec 9 ene), 6,8a:7,8 diepoxyisoquinoline (3 aza 11 oxatricyclo[ 1,6]undec 9 ene), bromine, decane, epoxide, ether, isoquinoline derivative, unclassified drug, article, carbon nuclear magnetic resonance, chemical analysis, chemical structure, proton nuclear magnetic resonance, reaction analysis, structure analysis, Wagner Meerwein rearrangement, X ray analysis
Publisher: 'American Chemical Society (ACS)'
Year: 2020
DOI identifier: 10.1021/jo0353684
OAI identifier:
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