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Tetraazapentalene Chemistry: Unexpected Intramolecular Electron Rearrangement Induced by Highly Reactive ψ ‐Dinitroso Substituents
Author(s) -
Huynh My Hang V.,
Hiskey Michael A.,
Chavez David E.,
Gilardi Richard D.
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200502342
Subject(s) - intramolecular force , chemistry , reactive intermediate , nitrogen atom , ring (chemistry) , rearrangement reaction , photochemistry , bond cleavage , intramolecular reaction , atom (system on chip) , stereochemistry , organic chemistry , catalysis , computer science , embedded system
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 .