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Wagner−Meerwein Skeletal Rearrangement of 3-Spiroannulated 6,8a-Epoxy- and 6,8a;7,8-Diepoxyisoquinolines (3-Aza-11-oxatricyclo[6.2.1.0<sup>1,6</sup>]undec-9-enes). Isolation and Identification of 5-Aza-2-oxatricyclo[6.2.1.0<sup>3,9</sup>]undec-3-enes

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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.

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2004-01-23
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