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Azide rearrangements in electron-deficient systems

Lang, Stuart and Murphy, John (2006) Azide rearrangements in electron-deficient systems. Chemical Society Reviews, 35. pp. 146-156. ISSN 0306-0012

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Abstract

The azide group has a diverse and extensive role in organic chemistry, reflected in the power of azide anion as a strong nucleophile, the role of organic azides as excellent substrates for cycloaddition reactions, the uses of azides as precursors of amines and nitrenes, and azide rearrangements known as the Curtius and Schmidt reactions. In recent years the scope of the Schmidt reaction has begun to be explored in depth, so that it now represents an important reaction in synthetic chemistry. This tutorial review analyses and summarises key recent developments in the field of Schmidt reactions.