Wagner-Meerwein skeletal rearrangement of 3-spiroannulated 6,8a-epoxy- and 6,8a;7,8-diepoxyisoquinolines (3-aza-11-oxatricyclo[6.2.1.0(1,6)]undec-9-enes). Isolation and identification of 5-aza-2-oxatricyclo[6.2.1.0(3,9)]undec-3-enes |
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| Authors: | Zubkov Fedor I Nikitina Eugenia V Turchin Konstantin F Aleksandrov Grigorii G Safronova Anastasia A Borisov Roman S Varlamov Alexey V |
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| Affiliation: | Organic Chemistry Department, Russian Peoples Friendship University, 6 Miklukho-Maklayia St., Moscow, Russian Federation 117198. fzubkov@sci.pfu.edu.ru |
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| Abstract: | The reactions of 3-acetyl-3-aza-11-oxatricyclo[6.2.1.0(1,6)]undec-9-ene and its 9,10-epoxy derivative with bromine and Ac(2)O/BF(3).OEt(2) under different conditions were studied. Unusual products of Wagner-Meerwein rearrangement bearing the olefin fragment (5-aza-2-oxatricyclo[6.2.1.0(3,9)]undecen-3-enes) were isolated and characterized by X-ray analysis. |
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