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The Trapping of Phenyldiazenes in Cycloaddition Reactions
Author(s) -
Fehler Stefanie K.,
Pratsch Gerald,
Heinrich Markus R.
Publication year - 2014
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.201406175
Subject(s) - cycloaddition , moiety , trapping , reactivity (psychology) , chemistry , ionic bonding , photochemistry , organic chemistry , ion , catalysis , biology , ecology , medicine , alternative medicine , pathology
The reactivity of phenyldiazenes was studied intensively in the late 1960s, but not much is known about their behavior under acidic conditions. Based on the formation of phenyldiazenes from phenylazocarboxylates, we herein describe how reactions of phenyldiazenes can be directed into ionic or radical pathways. Cycloaddition reactions with furans leading to pyridazinium salts represent the first examples for the direct trapping of phenyldiazenes with conservation of the NN moiety.