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A Masked 1,3‐Dipole Revealed from Aziridines
Author(s) -
Dauban Philippe,
Malik Guillaume
Publication year - 2009
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.200904941
Subject(s) - aziridine , cleavage (geology) , dipole , chemistry , ring (chemistry) , polar effect , medicinal chemistry , bond cleavage , stereochemistry , nitrogen , photochemistry , triple bond , double bond , polymer chemistry , organic chemistry , materials science , catalysis , fracture (geology) , composite material
Double agent : Switching the electronic nature of substituents on an aziridine ring induces the formation of the ring‐opened zwitterionic 1,3‐dipole through CN bond cleavage instead of the usual CC bond cleavage. This novel dipole reacts with alkenes, alkynes, nitriles, and carbonyl compounds to afford new types of [3+2] cycloadducts, thereby enhancing the diversity of nitrogen‐containing heterocycles accessible through 1,3‐dipolar cycloadditions. EWG=electron‐withdrawing group.