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

Fedor I Zubkov; Eugenia V Nikitina; Konstantin F Turchin; Grigorii G Aleksandrov; Anastasia A Safronova; Roman S Borisov; Alexey V Varlamov

doi:10.1021/jo0353684

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

J Org Chem. 2004 Jan 23;69(2):432-8. doi: 10.1021/jo0353684.

Authors

Fedor I Zubkov¹, Eugenia V Nikitina, Konstantin F Turchin, Grigorii G Aleksandrov, Anastasia A Safronova, Roman S Borisov, Alexey V Varlamov

Affiliation

¹ Organic Chemistry Department, Russian Peoples Friendship University, 6 Miklukho-Maklayia St., Moscow, Russian Federation 117198. fzubkov@sci.pfu.edu.ru

PMID: 14725457
DOI: 10.1021/jo0353684

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.