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40 Amines, Ammonium Salts, Amine N-Oxides, Haloamines, Hydroxylamines and Sulfur Analogues, and Hydrazines

DOI: 10.1055/sos-SD-040-00001

Schaumann, E.Science of Synthesis, (2009401.

General Introduction

This volume of Science of Synthesis covers the syntheses of compounds having a single bond between an sp3-hybridized carbon atom and a formally sp3-hybridized nitrogen substituent. As an aid to organization it has been split into two parts which are, respectively, Science of Synthesis, Volume 40a (Amines and Ammonium Salts) and Science of Synthesis, Volume 40b (Amine N-Oxides, Haloamines, Hydroxylamines and Sulfur Analogues, and Hydrazines). Among the product classes featured, one of the most prominent representatives is the aliphatic amines (Section 40.1); however, separate sections are devoted to propargylic (Section 40.1.2) and allylic amines (Section 40.1.3) for which special synthetic methods are available, or where special care must be taken to secure synthetic success. Similarly, compounds with more than one amino group or an additional phosphorus functionality are treated separately (Section 40.1.4), as are the obviously special small-ring amine derivatives aziridines (Section 40.1.5) and azetidines (Section 40.1.6). Furthermore, the amino group may be modified in the form of ammonium compounds or of N-ylides (ammonioalkanides; Section 40.1.7). There is also a wide range of functionalities where a parent amine structure is combined with one heteroatom. This type of compound is seen in nitroxyl radicals (nitroxides; Section 40.2), amine N-oxides (Section 40.3), N-haloamines (Section 40.4), hydroxylamines (N-hydroxyamines) in acyclic (Section 40.5) or in cyclic form (Section 40.6), and hydrazines, again in acyclic (Section 40.7) or in cyclic form (Section 40.8), as well as extended hydrazines (Section 40.9). Finally, amido derivatives of sulfur-derived acids, specifically of sulfanediol (Section 40.10), of sulfurous acid (Section 40.11), and of sulfuric acid (Section 40.12) are covered. Ammonium sulfonates, thiohydroxylamines, and aminosulfonium salts are also featured (Section 40.13). For a ready overview, these structures are compiled in Table 1.

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