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Geffken, D.; Köllner, M. A., Science of Synthesis, (2009) 40, 964.
Reduction of C-nitroso compounds to produce N-alkylhydroxylamines suffers mainly from the lack of a variety of starting materials, as well as the side reaction of the nitroso group with the hydroxylamine functionality to give azoxy compounds. For example, N-(2,2,4,4-tetramethylpentan-3-yl)hydroxylamine (144) is prepared from the corresponding nitrosoalkane by reduction with phenylhydrazine in methanol (Scheme 46).[188] Trifluoro(nitroso)methane is reduced by potassium hydrogen sulfite in diethyl ether/water to afford the N-(trifluoromethyl)hydroxylamine–diethyl ether complex (145) in 48% yield.[189]
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References
| [188] | Meeeeeeee, M. M.; Meeeeeeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 88, 88888. |
| [189] | Meeee, M. M.; Meeeeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
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- 8.Meeeee-Meee, (8888) 88/8, 8888.
- 8.Meeeee-Meee, (8888) 88/8, 8888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 88.
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