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Photochemistry of ortho ‐Phenoxymethyl‐Substituted Aryl Azides: A Novel Nitrene Rearrangement En Route to Isolable Iminoquinone Methides?
Author(s) -
Bucher Götz,
Korth HansGert
Publication year - 1999
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/(sici)1521-3773(19990115)38:1/2<212::aid-anie212>3.0.co;2-9
Subject(s) - nitrene , diethylamine , aryl , chemistry , nucleophile , azide , photochemistry , photodissociation , medicinal chemistry , organic chemistry , catalysis , alkyl
The answer to the question in the title is: probably yes. A surprising reaction is observed upon photolysis of aryl azide 1 in the presence of diethylamine. The iminoquinone methide 2 is isolable and is probably formed by a shift of the phenoxy group to the nitrene center followed by nucleophilic attack of diethylamine and elimination of phenol.