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40.1.1.4.2.4 Method 4: Hofmann, Curtius, Schmidt, and Lossen Rearrangements

DOI: 10.1055/sos-SD-040-00241

Purchase, R.; Sainsbury, M.Science of Synthesis, (200940395.

There are four mechanistically related procedures for the conversion of carboxylic acids and their derivatives into amines. These are the Hofmann, Curtius, Schmidt, and Lossen rearrangements, which all share isocyanate intermediates 155, or their equivalents,[‌188‌] which form the appropriate amines on hydrolysis, either under the reaction conditions or upon workup (Scheme 46).[‌188‌] In some cases, however, the intermediate isocyanates can be trapped by other nucleophiles so that a range of products become available. Although these procedures have long histories, they still have major roles to play in modern chemistry, especially as less drastic conditions and less dangerous reagent systems replace those that were originally employed {see Science of Synthesis, Vol. 31b [AreneX (X=N, P) (Section 31.28.1.33.4)]}.

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