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.
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.
Zubkov
Fedor I
FI
Organic Chemistry Department, Russian Peoples Friendship University, 6 Miklukho-Maklayia St., Moscow, Russian Federation 117198. fzubkov@sci.pfu.edu.ru
Nikitina
Eugenia V
EV
Turchin
Konstantin F
KF
Aleksandrov
Grigorii G
GG
Safronova
Anastasia A
AA
Borisov
Roman S
RS
Varlamov
Alexey V
AV