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[6.2.1.03,9]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 Ac2O/BF3·OEt2 under different conditions were studied. Unusual products of Wagner-Meerwein rearrangement bearing the olefin fragment (5-aza-2-oxatricyclo[6.2.1.0 3,9]-undecen-3-enes) were isolated and characterized by X-ray analysis.

Authors
Zubkov F.I. 1 , Nikitina E.V. 1 , Turchin K.F.2 , Aleksandrov G.G. 3 , Safronova A.A. 1 , Borisov R.S. 1 , Varlamov A.V. 1
Journal
Journal of Organic Chemistry
Number of issue
2
Language
English
Pages
432-438
Status
Published
Link
External link
DOI
10.1021/jo0353684
Volume
69
Year
2004
Organizations
  • 1 Organic Chemistry Department, Russ. Peoples Friendship University, 6 Miklukho-Maklayia St., Moscow, 117198, Russian Federation
  • 2 Center of Drugs Chemistry, All-Russian Inst. Chem./Pharma. Res., 7 Zubovskaya Street, Moscow 119815, Russian Federation
  • 3 N. S. K. Inst. Gen./Inorg. Chem., Russian Academy of Sciences, 31 Leninsky Prospekt, Moscow, 119991, Russian Federation
Keywords
Bromine; Derivatives; Olefins; Reaction kinetics; X ray analysis; Olefin fragments; Aromatic compounds; 5 aza 2 oxatricyclo[6.2.1.0 3,9]undec 3 ene; 6,8a epoxyisoquinoline (3 aza 11 oxatricyclo[6.2.1.0 1,6]undec 9 ene); 6,8a:7,8 diepoxyisoquinoline (3 aza 11 oxatricyclo[6.2.1.0 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
Date of creation
19.10.2018
Date of change
13.08.2021
Short link
https://repository.rudn.ru/en/records/article/record/3673/
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