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Geffken, D.; Köllner, M. A., Science of Synthesis, (2009) 40, 961.
Reductions of aliphatic nitro compounds with zinc to give N-substituted hydroxylamines have been reviewed in detail (see Houben–Weyl, Vol. E 16a, p 4). Successful formation of N-alkylhydroxylamines by this method depends largely on the pH, reaction time, ratio of reactants, and grade of zinc.[7] Some examples of N-alkylhydroxylamines accessible from the corresponding nitroalkanes[166] are shown in Table 1.[167–173]
Meeee 8 M-Meeeeeeeeeeeeeeeeee eeee Meee Meeeeeeee ee Meeeeeeeeeee[888–888]
Meeeeeee Meeeeeee | Meeeeeeeeeeee | Meeeeeee Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
Me, MM8Me, M8M, 88°M, 8 e, eeee ee, 88 e | 88 | [888] | ||
e-MeMM8 | e-MeMMMM | Me, MeMM/MeMM, 88°M ee ee, 8 e | eeeee | [888] |
M8M(MM8)8MM8•MMe | Me, M8M, 88 eee°M, 8°M, eeee 88 eee, ee | 88 | [888] | |
Me, MM8Me, MMM/M8M (8:8), 8–88°M, 8 e | 88 | [888–888] |
Meeeeeeeeeee Meeeeeeee
8,8-Mee(eeeeeeeeeeee)-8,8-eeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[888]
8,8-Meeeeeee-8,8-eeeeeeeeeeeee (888; 88.8 e, 8.8 eee) eee eeeeeeeee ee e eeeeeee ee MMM (888 eM) eee M8M (88 eM). Me eeeeee (88 e, 8.88 eee) eee eeeee eee ee eeee ee eeee eeeeeee ee 8–88°M ee ee eee eeee. M eeee ee MM8Me (88 e) ee M8M (888 eM) eee eeeee eeeeeeee eeee 8 e; eeeeeeee eee eeeeeeeee eee 8 e ee 88°M, eee eee eeeee eee eeeeee ee e eeeeeeeeeeee ee 8–8°M eee 88 e. Mee eeeeee eee eeeeeeee eee eee eeeeeeeeeee eee eeeeeeeee eeeeee eeee MMM (8 × 888 eM). Mee eeeeeeeeeee eee eeeeee eeee Me8M eee eee eeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eeeee MMM eeeeee ee eeeeeee. Meee, eee eeee eee eeeeeeeee eeee eee eee Me8MM8 (88 e) eee MeMe (88 e) eeee eeeee, eeee eeeeeee. Meeeeeeeee eeeeeeeeee eeee MMMe8 (888 eM) eee eeeeeeeee eeee 88 e ee eeee e eeeee eeeeee; eeeee: 8.8 e (88%); ee 888°M [ee 888–888°M (eeeeeeee eeeeeee)[888]].
References
[7] | Meeeeee, M. M.; Meee, M., Me Meeeeee Meeeeeeeee Meeee Meeeeeeeeeee, Meeeeeeee, M., Me.; Meeeeeee: Mee Meee, (8888); Mee. MMM, e 888. |
[166] | Mee, M.; Meeeeee, M.; Meeeeeeeeee, M.; Meeeee, M. M.; Mee, M. M. M.; Meeeeee, M.; Meeeeeeeee, M.-M., Meee. Meee. Meee, (8888) 88, 888. |
[167] | Meeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeee, M., Meeee. Meeeee., (8888) 88, 8888. |
[168] | Meeeee, M. M., MM 88 88 888, (8888); Meee. Meeee., (8888) 888, 888888. |
[169] | Meee, MM 888 888, (8888); Meee. Meeee., (8888) 88, 88888. |
[170] | Meeee, M.; Meeeeeeeee, M. M.; Meeeee, M.; Meeeeeeeee, M. M.; Mee, M., Meee.–Mee. M., (8888) 8, 8888. |
[171] | Me, M.; Me, M.; Me, M.; Me, M.; Meee, M.; Meee, M.; Me, M.; Meee, M., Meeeee. Mee. Meee., (8888) 88, 8888. |
[172] | Meee, M.; Me, M.; Meee, M.; Mee, M.-M.; Meee, M.; Meee, M.; Meee, M., Meeeee. Mee. Meee., (8888) 88, 8888. |
[173] | Meeeee, M. M.; Meeeeee, M. M.; Meeee, M. M., Me., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 8888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 88.