Tetraazapentalene Chemistry: Unexpected Intramolecular Electron Rearrangement Induced by Highly Reactive ψ-Dinitroso Substituents

Off with a bang: The thermally stable high‐energy 1 was prepared in a more efficient synthetic route. An unexpected ring scission of the tetraazapentalene T‐shaped isomer 1 (distinctive nitrogen atom arrangement indicated in blue) occurs through an intramolecular electron rearrangement activated by...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-11, Vol.44 (43), p.7089-7094
Main Authors: Huynh, My Hang V., Hiskey, Michael A., Chavez, David E., Gilardi, Richard D.
Format: Article
Language:English
Subjects:
azides
Crystallography, X-Ray
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Electrons
Heterocyclic Compounds, 2-Ring - chemical synthesis
Heterocyclic Compounds, 2-Ring - chemistry
Models, Molecular
Molecular Structure
nitrogen heterocycles
Nitroso Compounds - chemistry
reactive intermediates
rearrangement
ring opening
Stereoisomerism
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Summary:Off with a bang: The thermally stable high‐energy 1 was prepared in a more efficient synthetic route. An unexpected ring scission of the tetraazapentalene T‐shaped isomer 1 (distinctive nitrogen atom arrangement indicated in blue) occurs through an intramolecular electron rearrangement activated by highly‐reactive ψ‐dinitroso substituents of intermediate 2 to give 3.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200502342