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Organic Azides: An Exploding Diversity of a Unique Class of Compounds
Author(s) -
Bräse Stefan,
Gil Carmen,
Knepper Kerstin,
Zimmermann Viktor
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.200400657
Subject(s) - curtius rearrangement , chemistry , azide , staudinger reaction , ylide , click chemistry , cycloaddition , combinatorial chemistry , organic chemistry , computational chemistry , catalysis
Since the discovery of organic azides by Peter Grieß more than 140 years ago, numerous syntheses of these energy‐rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. In this Review, the fundamental characteristics of azide chemistry and current developments are presented. The focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles. Further reactions such as the aza‐Wittig reaction, the Sundberg rearrangement, the Staudinger ligation, the Boyer and Boyer–Aubé rearrangements, the Curtius rearrangement, the Schmidt rearrangement, and the Hemetsberger rearrangement bear witness to the versatility of modern azide chemistry.