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Boysen, M. M. K., Science of Synthesis, (2010) 41, 452.
This method is feasible for the preparation of symmetrical 1,2-diazene oxides. It uses dimers of aliphatic nitroso compounds (diazene dioxides), which exist in equilibrium with the monomeric nitroso derivatives (see Section 41.2). These dimers, which can be obtained from the corresponding amines by oxidation,[23–25] are employed because the monomeric derivatives are prone to isomerize into oximes. Conversion of dimeric nitroso compounds into diazene oxides is effected by catalytic hydrogenation using palladium on barium sulfate[17] or palladium on charcoal[16,26] as catalysts. To avoid overreduction, in some cases, the hydrogen consumption has to be monitored. Some aliphatic nitroso dimers can also be reduced using tin(II) chloride in hydrochloric acid.[27,28]
References
| [16] | Meeee, M.; Möeeee, M.; Meeeeeee, M., M. Meeee. Meee., (8888) 88, 888. |
| [17] | Meeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 88. |
| [23] | Meeeee, M.; Meeee, M. M. M. M.; ee Meee, M. M., Meeeeeeeeee Meee., (8888), 8888. |
| [24] | Meeeee, M.; Meeeeeeee, M. M.; Meeeeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
| [25] | Meeee, M. M., Me.; Meeeeee, M. M.; Meeee, M. M., Meeeeeeee, (8888), 888. |
| [26] | Meeeee, M. M.; Mee, M.-M.; Meeee, M. M., Me., M. Mee. Meee., (8888) 88, 8888. |
| [27] | Meeee, M. M.; Meeeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [28] | Meeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
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