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41 Nitro, Nitroso, Azo, Azoxy, and Diazonium Compounds; Azides, Triazenes, and Tetrazenes

DOI: 10.1055/sos-SD-041-00001

Banert, K.Science of Synthesis, (2010411.

This volume covers the synthesis of compounds containing a nitrogen functionality bonded to sp3-hybridized carbon atoms, as shown in Table 1. However, only in the cases of nitroalkanes, nitrosoalkanes, azides, and N,N-dihaloamines are the substituents R1 and R2 strictly limited to alkyl groups. Aliphatic diazonium compounds are divided into the subclasses of short-lived alkanediazonium compounds (Section 41.7.1) and the less labile alkenediazonium compounds (Section 41.7.2). Section 41.5 includes 1,2-dialkyldiazene 1-oxides and azoxy compounds carrying a vinyl group at one of the two different nitrogen atoms. In the cases of azo compounds (Section 41.6) and tetrazenes (Section 41.10), derivatives bearing aryl, vinyl, or acyl substituents at the nitrogen functionality are described along with such compounds having only alkyl groups. A few examples of rare tetraz-2-enes with lower symmetry than that shown in Table 1 are summarized in Section 41.10.2.1.5. The section on alkyltriazenes (Section 41.9) also includes derivatives with aryl or acyl groups at the nitrogen atom, while N-nitroamines bearing aryl or vinyl groups in addition to alkyl groups are discussed in Section 41.3. In the case of both of these nitrogen functionalities, hydrogen at the sp3-hybridized nitrogen (R2=H) is also possible. This is in contrast to N-nitrosoamines (Section 41.4), which are exclusively derived from secondary dialkyl- or alkyl(aryl)amines, or the corresponding acyl derivatives. N-Nitrosoamines originating from primary amines (R2=H) are unstable and lead to diazonium compounds (see Section 41.7).

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