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Please login to access the full content or check if you have access via31.28.1.33.4 Variation 4: Replacement of an Aromatic C—C Bond by a C—N Bond
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Scholz, U.; Schlummer, B., Science of Synthesis, (2007) 31, 1649.
The replacement of a C—C bond by a C—N bond can be achieved by the well-known Hofmann rearrangement. In a typical example, 2-benzoylbenzamide (197) rearranges to (2-aminophenyl)phenylmethanone (136) in good yield using sodium hydroxide and sodium hypochlorite (Scheme 213).[383]
Meeeee 888 Meeeeeeee ee (8-Meeeeeeeeee)eeeeeeeeeeeeeee ee Meeeeee Meeeeeeeeeeee ee 8-Meeeeeeeeeeeeeee[888]
Meeeeeeeeeeee, eeeee eeeeeeeee eeeeee, eeee ee eeeeee eeeeeee, eee ee eeee, ee ee eee eeeeeeeee ee e-eeeeeeeee (888) eeee e-eeeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee e-Meeeeeeee ee Meeeeee Meeeeeeeeeeee ee e-Meeeeeeee[888]
Mee Meeeeee eeeeeeeeeeeee ee eeee eeeeee eeee eee eee eeeeeeeee ee eeeeeeeeee eeee eee eeeeeeeeeeeee eeeee eeeeeeeee.[888] Me eee eeeee eeeeeeeee, eee eeeee eeeeeeee ee eeeeeeeee eeee eee eeeee eeeee eeeee eeeeee eeeee, eeeeeeeeeeeeee eeeee,[888] ee eeeeeeeeeeeeeeeeee eeeee.[888] Mee eeeeeeeeeeee eeeee eeee eeeeeeeeee ee eee eeeeeeeeee eeee eeeeeeeee ee eeeeeeee. Mee eeeeeeeeee ee eeee eeeeeeeeee ee eee eeeee. Mee eeeeeeeee ee eee Meeeeee eeeeeeeeeeeee eeee eeeeee eeeee ee eeeeeeeeeee eeee e eeeee-eeeeeeee eeeeeeee ee eeeeeeee eee eeeeeeeeee. Meeeeeeeeeeeeee eeee eeee eeee ee eee eeeeeeeeee ee eeeeeeeeee eee eeeeeeeeee ee eee eeeeeeeeeeee. Me eeee eee, 8,8-eeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeee eeee 8,8-eeeeeeeeeeeeeeee (888) (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee 8,8-Meeeeeeeeeeeeeee eeee 8,8-Meeeeeeeeeeeeeee Meeeeeee eee Meeeeee Meeeeeeeeeeee[888]
Mee Meeeeee eeeeeeeeeeeee eeeeeee e eeeeeee eeeeeee, eee ee eeee eeee eeeeeeeeee eeeee eee eeeeeee eeeeeeee eeee eeeeeeeee eeee. Mee eeeeeeee eee eeeeeeeeeeeee ee eeeeeeeee eeee eee eeeeeee ee eee eeeeeeeeeeeee eee e eeeeeeee ee eeee eeeeeeee. Me eeeee eeee eeeeeee, eee eeeeeeeee eeee ee eeeeeee eeeeeeeee ee eeee, eee eeeeeee eeee eeeeee eeeee eee e eeeeee eeee. Me ee eeeeeee eee eee eeeeeeeee ee eeeeeeeeee, 8-eeeeeeeeeeeee eeee eee ee eeeeeeeee eeee 8-eeeeeeeeeeeee (888) eeeee eeeeee eeeee eee eeeeeeeeeeee eeeeeeee eeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee 8-Meeeeeeeeeeee eeee 8-Meeeeeeeeeeee Meee eee Meeeeee Meeeeeeeeeeee[888]
M eeeeeee eeeeeeeeeee eeeeeeee ee eeeeeeee eeee eeeeeeeeee eeeee eee eeeeeee eeee eeeeee eeeee ee eeee eeeeeeeeeee. Meee eeeeeeeeeeeee eeeeeeee ee eeeeeee eeeeeeee ee ee eee Meeeee eeeeeeeeeeeee. Mee eeeeeee, eeeeeeeeeee-8-eeeeeeeeee eeee eeeee eeeeeeeeee-8-eeeee (88) eeee eeeeeee eeee eeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeeeee eeee ee 888–888°M (Meeeee 888).[888] Meeeeeeeeeeee, eee eeeeeeee eee ee eee ee eeeeeeeeeeee, eeee eeeeeeeeeee eee eee eeeee eeeeeeee.[888]
Meeeee 888 Meeeeeeee ee Meeeeeeeee-8-eeeee eeee Meeeeeeeeee-8-eeeeeeeeee Meee eee Meeeee Meeeeeeeeeeee[888]
M-Meeeeeeeeeeeeee-8-eeeeeeeeeee eeee eeeeeeeee e Meeeee eeeeeeeeeeeee eeee eeeeeeeeee eeeeeeeeee ee eee eeeeeeeeeeee eeeee eeee eeeeeeeeeeee eeee, eeeeeeee eeeeeee-8-eeeee (8) (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeeeee-8-eeeee eeee M-Meeeeeeeeeeeeee-8-eeeeeeeeeee eee Meeeee Meeeeeeeeeeee[888]
Mee eeeeeeeeeeeee ee eeeeeeeee eeeee eeeeeeee eeeeee eeeeeeeeee ee eeeeeeee eeeee ee eee Meeeeeee eeeeeeeeeeeee. Mee eeeeeeee ee eeeeeee eeeee eeeeeeeeee ee eee eeeee eee eeeeeeeeee eeeeee eeeeee eeeee eee eeeee. Mee Meeeeeee eeeeeeeeeeeee ee 8-(8-eeeeee-8-eeeeeeeeeeeee)eeeeeeee eeeee eeee eeeeeeeeee eeeeeeeeeeeee eee eeeeeeeeee eeeeeeeee eeee eeeeeeeeeeee eeeeeeeeeeee eeee eeeeee 8-eeeeee-8-eeeeeeeeeeeeee (888) (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee 8-Meeeee-8-eeeeeeeeeeeeee eeee 8-(8-Meeeee-8-eeeeeeeeeeeee)eeeeeeee Meeee eee Meeeeeee Meeeeeeeeeeee[888]
M eeeeeeeeee eeeeee eeeeeeeee ee eee Meeeeeee eeeeeeeeeeeee ee eee eeeeeeeee ee eeee eeeeeeeee eeee eeeeeeeeeeeeeeeeee eeeeeee. Meeee eeeeeeeeeeeee, eee eeeeeeeeeeee eeeee ee eeeeeeee eeeeeee ee eee eeeeeeeeee, ee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee eeeee eeee eeeeeeeeeeeeeeeeee eeeeeee ee 8°M ee eeeee M-eeeeeeeeeeee (888) (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee M-Meeeeeeeeeee eeee Meeeeeeeeeee Meeee eee Meeeeeee Meeeeeeeeeeee[888]
Me eeeeeee eeeeeeeee ee eee Meeeeeee eeeeeeeeeeeee, eeee eeeee eeeeeeeeeeeeeeeee eee eeeeeee eeee Meeeeeee eeeeeeee. Meeeeeee eeeeeeee eee eeee eeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeee eeeeeeeeeeeeee eeeeeee, eee eeee eee eeee eeee ee eeeeeeee eee eeeeee. Meeeeeeee, eeee eeeeeeee eeeeeeeeee α-eeeeeeeee eeee eee M-eeeee eeeeeeeeeee. Mee eeeeeeeee eeeeeeeeeeee eee eeeeee ee eeeeee ee eeeeeeeeeee eeeee eeeeeeeeeeeeeeeeee eeeeeee, ee eeeee eeeeeeeee eeeee e Meeeeeee eeeeeee. Mee eeeeee eeee ee eeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee M-eeeeeeeeee eeee eeeeeeeeeeeeee eeeeeee eee eeeeeeeee eeeeee eeee eeeeeeeeeeeeeeeeee eeeeeee ee eeeee M-(8-eeeeeeeeeeee)eeeeeee (888) (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee M-(8-Meeeeeeeeeee)eeeeeee eeee Meeeeeeeeeee M-Meeeeeeeee eee Meeeeeee Meeeeeeeeeeee[888]
Meeeeeeeeeee Meeeeeeee
e-Meeeeeeee (888); Meeeeee Meeeeeeee:[888]
M eeeeeeeeee ee e-eeeeeeeee (8.8 e, 8.8 eeee) ee M8M (88 eM) eee eeeeee ee 88°M eee e eeee ee MeMeM8 (8.8 e, 8.8 eeee) eee MeMM (8.8 e, 88 eeee) ee M8M (8 eM) eee eeeee. Mee eeeeeee eee eeee eeeeee ee 888°M eee eeeeeeee eee eeeeeeeee eee 88 eee. Mee eeeeeeeee eeeeeee eee eeeee eeeeeeeee eee eee eeeeeeeeee eee eeeeeeeee eeee Me8M (8 ×), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 8.88 e (88%).
References
[383] | Meeeee, M. M., M. Meee. Mee., (8888), 888. |
[384] | Meeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeee, M., Meee. Meee., (8888), 8888. |
[385] | Meeee, M. M. M., Mee. Meeee. (M. M.), (8888) 8, 888. |
[386] | Meeeeeeee, M. M.; Meeeeeeee, M. M., Meeee. Meeeee., (8888) 8, 888. |
[387] | Meeeeee, M.; Meeeeeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
[388] | Meeeeee, M. M.; Meeeee, M. M., Meeeeeeee, (8888), 88. |
[389] | Meeee, M. M.; Meeeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[390] | Meeeee, M. M.; Meeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[391] | Meeeeee, M. M.; Meeeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[392] | Meeeeeee, M.; Meeeeeeeee-Meeeeee, M.; Meeeeeeeee, M., Meeeeeeeeeee, (8888) 88, 8888. |
[393] | Mee-Meï, Me. Me.; Meeee, M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[394] | Meeeeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[395] | Meeeeee, M.; Meeeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.