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Reissig, H.-U.; Dugovicč, B.; Zimmer, R., Science of Synthesis, (2010) 41, 327.
The reaction of tertiary nitrosoalkanes with amines provides a general method for the synthesis of azoxy compounds with two different substituents (unsymmetric azoxy compounds).[575–583] The original procedure for the preparation of N,N′-dialkyldiazene N-oxides 318 was based on the condensation of 1-chloro-1-nitrosocyclohexane with the rather unstable dihaloamines 317 (Scheme 103).[580]
Meeeee 888 Meeeeeeeeee-Meeee Meeeeeeee ee M,M′-Meeeeeeeeeeeee M-Meeeee[888]
Mee eeeeee eee eeee eeeeeee eeeeeeee eee ee eeee eeeeeeeee ee eeeee eeeeeeeeeee eeeee eeeeeeee eeee ee eeeeeeee eeeeeeeeee 888,[888–888] eeeeee eeeeeeeeeeee,[888] ee (eeeeeeeeeeeee)eeeeeee.[888] Mee eeeeeeeeeeeee eeeeeeeee ee M,M′-eeeeeee-,[888] M′-[α-(eeeeeeeeeeee)eeeee]-,[888] eee M′-eeeeeeeeeeeeeeeee M-eeeeee 888[888,888] eee MMM-eeeeeeeeeeeeeee eeeee[888] 888 eee eeee eeeeeeee eeeeeeee eeee eeeee eeeeeeeee 888 eee eee-eeeeeeeeeeeeeeeeeee 888. Meeeeeeee eeee eeeeeeee 888 ee eeeeeeee eee eee ee eeee eeeeeeeee ee eee eeeeeeee eeeeeeeeeee eeeeeeeeeee (Meeeee 888). Meeeeeeeeeeee, eee eeeeeeee ee eeeeeee eee-eeeeeeeeeeeeeeeeeee eeee eee(eeeeeeee)eeeeeee ee eee eeeeeeee ee eeeeeeee 888 eeeeeee ee eeeeee eeeeeeeeeee ee eee eeeeeee eeeee ee eeeeeee ee eee eeeeeeee eeeeeeee ee 88–88% eeeeee.[888]
Meeeee 888 Meeeeeeee ee Meeeeeeeeee Meeee Meeeeeeee[888–888]
| M8 | M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|---|
| Me | Me | Me | 88 | [888] |
| Me | Me | Me | 88 | [888] |
| MM8MMMe8MMM8 |  |
88 | [888] | |
| Me | Me | |
88 | [888] |
| MM8MMMe8MMM8 | |
88 | [888] | |
| MM8MMMe8MMM8 | |
88 | [888] | |
| MM8MMMe8MMM8 | MM8Me | 88 | [888] | |
Meeeeeeeeee, e eeeeeee ee M-eeeee-eeeeeeeeeee M′-eeeeeeeeeeeee M-eeeeee eeee eeee eeeeeeee ee eeeeeeee ee eeeeeeeeeeeeee eeeeee eeee eeeeeeeeeeeeeeeeeeee ee eeee e eeeeeeee–eeeeeeeeeeeee eeeeeee (Meeeee 888).[888] Mee eeeeeeee eeeeeeee eeeeeee ee 8–88°M eeee eeeeeeeee eeeeeeeeeeeeee eee eeeeeeee. Me eee eeeee eeee, eeeeeee ee eeeeeeeeeeeee ee eeeeeeeee ee eeeee ee eeeeee eeeeeeeeee eeeeeee ee eee eeeeeeee eeee eeeeeee eeeeeeeeeeeeee.
Meeeee 888 Meeeeeeee ee M-Meeee-Meeeeeeeeee M′-Meeeeeeeeeeee M-Meeeee[888]
Meeeeeeeeee ee eeeee-eeeeeeeeeee eeeeeeee eeeee 888 eeeeeeeee e eeeeeee eeeeee ee eeeeeeee eeeeeeeee eeee eeee ee eeeeeeeee eeeeeeee eeeeeeeee ee eee eeeeeee eeeeeeeeeeee eeeeeeeeee.[888] Me eeeeee e eeeeeeeeeeee ee ee eeeeee-eeeeeeeeee eeeeeeeeeeee eeeeeeee ee eeeeeeeeeeeee 88, eeeeeeeeeee eeeee eee-eeeee eeeeeeeeee (888 ee, 888-M eeeeeee eeee eeeeeeee eeeeeee eeeeeee eeeeeeeee eeeeeeee) eeeee eeeee eeeeeeee 888 eeeeeeee eeee eeeeee ee eeeeeeeeee 888 (Meeeee 888). Me eeeeeeee, eeee-eeeee eeeeeeeeee (888 ee, 8 MM eeeeee eeeeeeee eeeee) ee eeeeeeeee eeeeeeeee eeeee eeeeeeeeee 888 ee eee eeeee eeeeeee (88%) eee eeeeeeeeeeee 888 ee eeee 88% eeeee ee eee eeee ee eeeeeeeeeeee eeeeeee. Meeeeee eeeeeee ee eeeee eeeeeeeee ee eee eee-eeeee eeeeeeeeeee eeee eeee eeeeeeee eee eee eeeeeeee ee eeeeee-eeeeeeeeee eeeeeeee.
Meeeee 888 Meeeeeeeee ee 8-Meeeeeeeeee Meeee ee eee Meeeeeee ee e Meeeeeeeeeeee[888]
| Meeeeeeeee | Meeee (%) | Mee | 888 | 888 |
|---|---|---|---|
| 8.88 M e-MeMM, eν (eee eeeee), M8 eeeeee, MeMM | 88 | eeeee | [888] |
| 8.88 M e-MeMM, eν (eeee eeeee), M8 eeeeee, MeMM | 88 | 88 | [888] |
| 8.88 M e-MeMM, eν (eee eeeee), M8 eeeeee, MeMM | 88 | eeeee | [888] |
| 8.88 M e-MeMM, eν (eeee eeeee), M8 eeeeee, MeMM | 88 | eeeee | [888] |
Meeeeeeeeeee Meeeeeeee
(M)-8-Meeeee-8-(8-eeeeeeeeeee-8-ee)eeeeeee Meeee (888, M8 = M8 = M8 = Me); Meeeeee Meeeeeeee:[888]
M eeeeeee ee eeeeeeeeeeeee 888 (M8 = M8 = Me; 8 eeee), eeeee 888 (M8 = Me; 8 eeee), eee eeeeeeeeeeeeeeeeee eeee (888; 8 eeee) ee eee MM8Me8 (88 eM) eee eeeeeee eee 8 e ee 8°M eee eee 88 e ee ee. 88°M. Mee eeeeeeeeeee eeeeee eee eeeeeee ee eeeeeeeeee eee eeeeee eeee MM8Me8 (8×88 eM). Mee eeeeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeee (ee 888°M/8.88 Meee); eeeee: 88%.
References
| [575] | Meeeee, M. M.; Meeeeeeeeee, M. M.; Meeeeeeeee, M. M.; Meeeeeeee, Me. M.; Mee’eeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 8888; Meee. Meee. Mee. MMMM, Mee. Meee. Mee. (Meee. Meeeee.), (8888) 88, 8888. |
| [576] | Mee’eeeee, M. M.; Meeeeeeee, Me. M.; Meee, M. M.; Meeeeeeee, Me. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 888; Meee. Meee. Mee. MMMM, Mee. Meee. Mee. (Meee. Meeeee.), (8888) 88, 88. |
| [577] | Meeeee, M. M.; Meeeeeeeeee, M. M.; Meeeeeeee, Me. M.; Mee’eeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 8888; Meee. Meee. Mee. MMMM, Mee. Meee. Mee. (Meee. Meeeee.), (8888) 88, 888. |
| [578] | Mee’eeeee, M. M.; Meeeeeeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 8888; Meee. Meee. Mee. MMMM, Mee. Meee. Mee. (Meee. Meeeee.), (8888) 88, 8888. |
| [579] | Meeeee, M. M.; Meeeeeeeeee, M. M.; Meeeeeeee, Me. M.; Mee’eeeee, M. M.; Meeeeeeeeeeee, M. M.; Meeeeeeee, Me. M., Mee. Meee. Meee, Mee. Meee., (8888), 8888; Meee. Meee. Meee., (8888) 88, 8888. |
| [580] | Meeeee, M.; Meeeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [581] | Meeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [582] | Meeeeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [583] | Meeee, M. M.; Me, M.-M.; Meee, M.; Meee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [584] | Meeeeee, M. M.; Meeee’ee, M. M.; Mee’eeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 8888; Meee. Meee. Mee. MMMM, Mee. Meee. Mee. (Meee. Meeeee.), (8888) 88, 8888. |
| [585] | Meeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
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