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Please login to access the full content or check if you have access via31.28.1.33.2 Variation 2: Replacement of an Aromatic C—H Bond by a C—N Bond
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Scholz, U.; Schlummer, B., Science of Synthesis, (2007) 31, 1645.
A very exotic approach to arylamines is the Fischer–Hepp rearrangement[365] of N-nitrosamines to 4-nitrosoanilines under acidic conditions. N-Nitrosodiphenylamine (182) rearranges to 4-nitroso-N-phenylaniline (15) in 60% yield using diethyl ether saturated with hydrogen chloride at 0°C (Scheme 199).[366] The methodology can be extended to other systems such as carbazoles.[367]
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Meeeee 888 Meeeeeeee ee 8-Meeeeee-8-eeeeeeeeeeee eeee 8-Meeeeeeeeeeeee[888]
Meee eeeee eeeeeeeeee, eeee ee eeeeeeee eeeeee eeeee eee eeee eeeeeeeeeeee, eee ee eeee ee eeeeeeeee eeeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeee-8,8-eeeeeeee. Mee eeeeeee, eeeeeeeeeeeeeee eeee eeeeee ee 888°M ee eeeeeeeeeeee eeeeeeeeeeee eeee eeeee eeeeeee-8,8-eeeeeee (88) (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeeeee-8,8-eeeeeee ee Meeeeeeeeeeee ee Meeeeeeeeeeeeee[888]
M,M′-Meeeeeeeeeeeeeee eeee eeee eeee eeeeeeeee eeeeeee eee eeeeeee eee ee-eeeeee eeeee-eeeeeeee eeeeeeeeeeeee eeee eeeeee ee eeeeee eeeee. Me eeee eee, M,M′-ee-8-eeeeeeeeeeeeee eeeeeeeeee ee 8-eeeeee-M8-(8-eeeee)eeeeeee-8,8-eeeeeee (888) ee eeeeeeee eeeee (Meeeee 888).[888]
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References
[365] | Meeeeee, M.; Meee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
[366] | Meeeeeeeeee, M.; Meeeeeeeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
[367] | Meeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[368] | Meee, M. M.; Meeeeeee, M., M. Meee. Mee., (8888), 8888. |
[369] | Meeeee, M.; Meeeeee, M. M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
[370] | Meeeeeeeee, M.; Meeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 888. |
[371] | Meee, M. M.; Meee, M. M.; Meeee, M. M.; Meeeeeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 888, 888888. |
Meeeeee Meeeeeeeeee
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- 8.Meeeee-Meee, (8888) 88/8, 888.