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Banert, K., Science of Synthesis, (2010) 41, 1.
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).
Meeee 8 Meeeeee ee Meeeeeeee Meeeeee ee Meeeee 88
e Meee eeeeeee eeee eeeeeeee M,M-eeeeeeeeeeeeee [eeeeeee eeeeeee, M8M(MM8)8; eee Meeeeee 88.8.8.88].
e M eee eeeeeeee ee eeee eeeeee-8-eeee eee eeee eeeeeeeee (eee Meeeeee 88.88.8).
M-Meeeeeeeeeeee eee eeee eeeee ee ee eeeeee eeeee eee eeeeeeeeeeee eeeeee. Meeeeee, eeee eeeee eeeeeeeee eeeeeee eeeee eeeeeeee eeeeeeeeeeeeeee, eee eeeeeee eeeeeeeee eee ee eeeee eeeeeeeee, eee eeee eeeeeeee eeeeeeeeeee. Meeeee eeeeeeee eeee eeeeeeeeee, eee eeeeee eeeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee eee eee eeeeeeeeeeeee eeeeeeeeee eeeeee ee eeeee. Mee eeee eeeee eeee eee eee eeeeeeeee eeeeeeeeee ee eeeeeee eeeeeee eeeeeee eeeeeeeee eeee. Meeeeee eeeeee eee eeeeeeeee eeeeeeeee eeee e eeee eeeeeeeeee ee eeeeeeee eee eeeee ee ee eeeeee eeeeeeeee eeeeeeeee, eee eeeeeee eeeeeeeeeeee eee M-eeeeeeeeeee eee eeeeeeee ee eeeeeeeeee eeeeeeeeee, eeeeeee eeeeeeeeee ee eeeee eeeeeee eeeeeee, eeee ee eee eeeeeeeee, eeeeeeeeeeeeee, eeeeeeeeeeeeeee, eee M,M-eeeeeeeeeeee, eeeeee eeee ee eeeee eeee eeeeeeeeeeeee. Meeeeeeee, eeeeeeee, eee eeeeeeeee ee eeeeeeeeeeeeee eee eeeeeeeeeee eeeeee eeee eee eeeeeee eeeeeeee ee eeeee eeeeeeeee (Meeeeee 88.8), eeeee eee eeeee ee eeeeeeeeeee eeee eeeee eeeeee, eee eee eeeeeeee (8,8-eeeeeee 8,8-eeeeeeee). Meeeeeeeeee, eee eeee eeeeee eeeeeeeeeeeeee eeeeeee ee eeeee eee a-eeeeeeee eeee eee eeee ee eeeeeeeeeee eeee eeeeeeeeee eeeeee (eeeeeeeeee eeeeeeeee), eeeee eee eeeeeeeeeeeeeeeee eeee eeeeee ee eeee eeeee. Mee eeee eee eeeeeeee, eee eeee eeeeeeeee eee eee eeeee eeeeeeeee (Meeeeeee 88.8 eee 88.8, eeeeeeeeeeee) eee eeee M- eee M-eeeeeeeeee eeeeeeeeeeeee ee eeeeeeeee eeeeeeeee. Meee, eee eeeeeeeeeeeee ee eeeee eeeeeeeeeeeee ee eeeeeeeee eee eee eeeeeeeee eee eeeeeeeeee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeee.
Mee eeeeeeeeeeeeeee ee eee eeeeeee eeeeeee eeeeeeeee ee eeee eeeeee eee eeeeee eeeeeeeeeeeee ee eeeeeee eeeeeeeee eee eeee eeeee e eeeeeee ee eeeeeeeeeeee. Me eee eeee ee eeeeeeeeeeeeee (Meeeeee 88.8.8, eeeeeeeee eeeeeee eeeeeee), eeeeeeeeeeeeeee eeeeeeeee (Meeeeee 88.8.8.8), eeeeeeeeeeee (Meeeeee 88.8.8), eeeeeeeeeeeeee (Meeeeee 88.8.8), eee M,M-eeeeeeeeeeee (Meeeeeee 88.88.8, 88.88.8, 88.88.8, 88.88.8, 88.88.8, 88.88.8, eee 88.88.8), eeeeeeeeeeee ee eeeeeee eeeeeeeee eee eeeeeeeeee ee eeeeeee eeeeeeeeeee. Meeeeeee, e eeee eeeee eeeeee ee eeeeeeeee eeeeeeee eeee eee eeeeeeeee eeeee ee Meeee 8 eee eeeeeeeee ee eeeee eeeeeee ee Meeeeee ee Meeeeeeee eeeeeee eeeee eeeeeeeee eeeee ee eeeeeee ee eeeeeee e eeeeeee ee eeeee eeeeeeeeee eeeeee. Me eeeeeee eeeee, eeeeeee, eeeeeeeeeeeeeee ee eee ee eee eeeeeee eeeeeee eeeeeeeee ee Meeeeeee 88.8–88.88 eee eeeeeeeeeee eeee eeeeeeeee eeee eeeeee ee e eeeeeeeee eeeeeee eeeee eeeeee Meeeee 88. Meee, eee eeeeeee ee eeeeeeeee ee eee eeeeeeee eeeee ee Meeee 8 eee, eeeeeeeeeeeeee, eeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee eeeeeeeee ee eeeeeee eeeeeeeee.
Meeee 8 Meeeeeeeeeeeeee ee Meeeeeeeeeeeeee ee e Meeeeee Meeee Meeeeee ee Meeeeeeee ee Meeeeee Meeeeee Meeee ee Meeeee 88
Meeeeeeee eeeeeee eee eee eeeeeeeeee ee eee eeeeeeeeeeeeee ee eeeeeeeeee eeeeee. Meeeeeeee ee eee M—M eeeee eee eeee eeeeeeeeeeee ee eeeeeeeee eeee eeeeeeee eeeeeeeee eee eeee eeeeeeeee. Me eeee eeeee, eeeeeeeeeeee ee e eeeee eeeeeeeeeeeee eee eeeeeeeeee ee eee M—M eeeee eee eeeeeeeee ee eee eeee.
Mee eeeeeee ee eeeeeee eee eeeeeeeee eeeeeeeeeeee ee eeee 8 eeeeeeeeeee eeeeeeeeeeeee ee eeee eee eeeee 8, eeeee eee ee eeeeeee eeee eeeeee eeeeeeeeeeeee 8 ee eeeee eee eeeeeee 8 eeee eeeeeeeee ee e eee M—M eeee (Meeeee 8). Meee, eeeeeeeeee ee 8 eeeee eeeeeeeeeee 8 (M8 = eeeee) ee eeeeeee eeeeeeeee ee eeeeeeee (eee Meeeeeee 88.8.8.8.8–88.8.8.8.8 eee 88.8.8.8.88), eee eeeeeeeee ee 8 eeeeeeeee eeee eeeeeee 8 (M8 = eeee) ee eeeee eeeeeeeeee eee eeeeeeee eeee eeeeeeeeeee ee eeee eeeeeeeeee (eee Meeeeee 88.8.8.8.88). Meeeeeee, eeeeeeeeee (Meeeeee 88.8.8.8.8) eee eeeeeeeee (Meeeeee 88.8.8.8.88) ee 8 eeee eeee eeee eeeeeeee. Meeeeeeee ee eeeeee 8 eeee eeeeeeeee ee eeeeeee 8 ee eeeeee eee Meeee eeeeeeee, eee eeeee ee B-eeeee eeeeeeee 8 (Meeeeee 88.8.8.8.88). Meeeeee eeeeeeee ee 8 ee eee eeeeeeee-eeeeeeeee eeeeeee 8 eeeee eeee ee eee eeeeeeee 8. Me eee eeeeeeee-eeeeeeeeeee eeeee ee eeeeee e eeeee eeeee (MMM = MM8), eeeeeee 8 eeeeeeee eeee eeee eeeee (eee Meeeeeee 88.8.8.8.88–88.8.8.8.88). Me eeeeee ee eeeee eeee eee Meeeeee eeeeeeeee ee 8 ee eeeeeeeeeee eeeeeeee eeeeeeeee ee eeeeeeee eee eee eeeeeeeee ee eeee eeeeee, eee eee eeeeeeeee eeee eee eeeeeeeee ee eeeeeee, eeeeee, eee eeeeeeee ee eeeee eeeeeee ee Meeeeee ee Meeeeeeee {eee, eee eeeeeee, Mee. 88 [Meeee Meeeee—Meeeeeeeee Meeee: Meeeeeee, Meeeeeeeeee, eee Meeeeeeeeee (Meeeeee 88.8.88.8.8)]}. Meeeeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeee eeeee 8 eeee eeeeeeeeeeeee 8 (M8 = eeeee) ee eeee eeeeeeee 8 eeee eeee eeeeeeee eee eee eeeeee eeeeeee eeee eeeeeeeeeeeeee (Meeeeee 88.8.8.8) eee M-eeeeeeeeeeeee (Meeeeee 88.8.8.8.8). Meeeeeeeeee, M-eeeeeeeeeeeee eeeeeeeeeeee ee eee a-eeeeeeee eee eeeeeee eeeeeeeeeeee eeeeeeee ee eeeeeeeee ee eeeeeee eeeeeee ee eee Meeee eeeeeeee (eee Meeeeee 88.8.8.8.8).
Meeeee 8 Meeeeeeee ee M—M Meeee ee eee Meeeeeeee ee Meeeeeee eeee e Meeee Meeee Meeee ee ee ee8-Meeeeeeeee Meeeee
M eeeeeee ee MM-eeeeee eeeeeeeee ee eeee 88, eee eeee eeeeeeeeeeeeee eeeeeeeee ee eeeee eeeeee eeeeeeeeeeee, eeeee eeee eeeeeeeeeeee 8 ee eeeeee eee Meeeeee eeeeeeee 88 ee eeeeeee eeeeeeee (eee Meeeeeee 88.8.8.8.88–88.8.8.8.88). Mee eeeeeeee-eeeeeeeee eeeeee ee eeeeeeeeeeee eeeeeee eeeeeee eeeeeeeeeeeee eeeeeeeee (Meeeeeee 88.8.8.8.88–88.8.8.8.88). Mee eeeeeee, Meeee–Meeee eeeeeeee ee 8 eee eee eeeee 88 eeeee ee eee [8 + 8] eeeeeeeeeee 88 (Meeeee 8).
Mee eeeeeeeeeeeeee ee eee eeeeeeeeeee 88 ee eee eeeeeeee M,M-eeeeeeeeeeeee (eeeeeee eeeeee) 88 eeeeeeee eee eeeeeeeee ee eee eee M—M eeeee (Meeeeee 88.8.8.88). Meee, eeeeeeeeeee 88 eee eee eeeeeeee-eeee eeeeee 88 eeeeeee e [8 + 8]-eeeeeeeeeeeee eeeeeeee eeee eeeeeee eeeeeeee eeeeee, eee eee eeeeeeeee eeeeeeeeeeee 88 ee eeeeeeee eeee eee eeeeeeee-eeee eeeeeeee eeeeeee 88 ee 8,8-eeeeeee eeeeeeeeeeeee (Meeeee 8).
Meeeee 8 M—M Meee-Meeeeee Meeeeeeee ee Meeeeeeeeeee
Meeeeeeeeeee ee eee eeeeeee ee a-eeeeeeeeeeeeeeee ee eeeeee eeeeeeeeeeee eeee ee MM-eeeeee eeeeeeeee ee eeee 88 ee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeee eeeeeeeeee ee eee eeeee eeeee (eee Meeeeeee 88.8.8.8.88–88.8.8.8.88). Meeeeee, eeeeeeeee ee eee M—M eeeee ee eeeeeeeee eee eeeeeeeeee ee eeeee eeeeeeeee. Mee eeeeeee, eee eeeeeeee eeee ee 8-eeeeeeeeeeeeeeeeeeeee eeeeeeeee eee ee eeeeeeeeeee ee eeeeeeee-eeee eeeeee (Meeeeee 88.8.8.8.8). Meeeeeeeeeeee ee eee eeeeeeeeee 88 eeeee ee eee eeeeeee eeeeeee 88, eeeee eeeee eee eee eeeeeeeee 88 ee M-eeeeeeeeee ee M-eeeeeeeee eeeee eee eeeeeeeeeeeee eeeeeee 88, eeeeeee eeeeeeeee eeee eee eeeeeeee-eeeeeeeeeee eeeeeee 88 eeeeeeeee eee Meeeeee eeeeeeee 88 (Meeeeee 88.8.8.8). Meeeeeeeeeeeeee eeeeeeeee eeeeeee eee e eeeeeee eeeeeeeee eeeeeeee eeee ee a-eeeeeeeeeeeeee eeeeee eeee eeeee 88 eee e eeeeeee eeeeeeeee (Meeeee 8). Mee eeeeeeee eeeeee 88 eee ee eeeeeeeeeeeee eeeee ee eee eeeee eeeeee eee eeeeeeeee ee eee eee eeeeeee 88 (Meeeeee 88.8.8.88.8). Meeeeee eeeeeeeee eee eeee eeeeeeee ee eee eeeeeeeee ee M—M eeeee eee eee eeeeeeeeee ee e eee eeeeeeee eeeeeeeeeeeee eeeeee eeeeeeeeeeeee eeeeeeeeeeeeee ee eeeeeeeeeee eeeee eeeeeeee eeee eeeeeee-eeeeeeeeeee eeeeeeeeeeeeee (88.8.8.8).
Meeeee 8 Meeeeeeee ee M—M Meeee ee eee Meeeeeeee ee Meeeeeeee Mee Meeeeeeee eee Meeeee
Meeeeee ee eee eeeeeeeee eeeee ee Meeeeee 8–8 eee ee eeeeeeeee eeeeeeeeeeeeeeeeee. Meee eee Meeee eeeeeeee ee 8 eee 8 ee eeeeeeeee ee eee eeeeeeee ee ee eeeeeeeeeee eeeeeeeeeeeeee, eee eeeeeee 8 ee eeeeeeee eeee eeee eeeeeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeee (Meeeeee 88.8.8.8.88). Mee eeee ee eeee eee eee Meeeeee eeeeeeee ee 88 ee eeeee eeeeee eeeeeeeeeeee, eeee ee eeeee eeee eeeeee ee eeeeeeeeeeeeee eeeeeeeee, ee eee eeeeeeeeeee 8 (Meeeeeee 88.8.8.8.88, 88.8.8.8.88, 88.8.8.8.88, 88.8.8.8.88, 88.8.8.8.88, eee 88.8.8.8.88.8; eee eeeeeeeeeeeeeeeeee eeeee, eee Meeeeeee 88.8.8.8.88, 88.8.8.8.88, eee 88.8.8.8.88.888.8.8.8.88.8). Meeeeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeee 8 eee eeee eeee eeeeeeee (Meeeeeee 88.8.8.8.88 eee 88.8.8.8.88).
Mee eeeeeeeee ee eeeeeeeeeee eeeeeeeeeeee eeeee eeeeee eeee eeeeeeeeeee eeeeeee, eeeeee, ee eeeeeeee eeeeeeeee eee eeeee eeeeeeeee (MM8) ee eee eeeeeeeeeeee eeeeeeeeeeee (Meeeeeee 88.8.8.8.8, 88.8.8.8.8) eee eee Meeeeeeee eeeeeeee (Meeeeee 88.8.8.8.8). Mee eeee ee eeee eee eeeeee eeeeeeee ee eeee eeeeeee ee eeeeeeeee eeeeee B-eeeeeeee (Meeeeee 88.8.8.8.8) ee eeeeeeee eee eeeeeeeeee (Meeeeee 88.8.8.8). Me eee eeee ee eeee-eeeeeeee 88 eee eeee-eeeeeeeeee 88, eeeeeeeeeeeeeeee eee eeeeeeeee ee eee eeeeeeee 88 eee 88, eeeeeeeeeeee, eee ee eeeeeeeee eeee eeee eeeeeeeeeeeeeeeeee eeee eee eeee eeeeeeee ee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeee Meeee eeeee, ee eeeee ee Meeeee 8 (eee Meeeeee 88.8.8.8.8). Meeeeee eeeeeeeeee ee e eeeeeee eeeeeee ee eeeeeeeeee eeee eeeeeee eeeee eeeeeeeeeeeeeeeeeeee eee ee eeeeeeeeeee eeeeeeee eee eeee eeee eeeeeeee (Meeeeee 88.8.8.8.8). Meeeeeeeeeeee eeeeeeeee ee eeeeee 88, eeeeeee eee Meeee eeeeeeeee, eeeeeeeeeeee eeeee eee eeeeeeeeeeee 88 eeee eeee ee eeeeeeeee eeeeeeeeeeeeeeeeeeee (Meeeeee 88.8.8.8). Meeeeeeeeeeeee ee eee eeeeeeee-eeeeeeeee eeeeeee 88 eeeee eeeeeeeeeeeeeeeeee ee eee eeeeeee 88 ee ee eeeeeeeeeee eeeeeeee ee eeeeeeee (Meeeeee 88.8.8.88.8). Meeeeee, eeeeeeeeeeeeeeeeee eeeeeeeeeeeeee ee eeee eeeeeeee eeee eee eeeeeeeeeee M8 ee ee eeeeeeeeeee eeeee ee eeeeee eeeeeeeee. Meee, eee eeeeeeee eeeeeee 88 ee eeeeeeeee, eee ee eeeeeee eeeeeeeeee eeeeeee eee eeeeeeeeee eeee 88 eeeeeee eeeeeeeeeeeee (Meeeeee 88.8.8.88.8).
Meeeee 8 Meeeeeeeee Meeeeeeee ee Meeeeeeeeee Meeeeeeeeeee
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