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Purchase, R.; Sainsbury, M., Science of Synthesis, (2009) 40, 391.
A seemingly related reaction is known as the Reilly–Hickinbottom rearrangement in which an alkyl(aryl)amine is heated at 200–350°C with a metal halide, phosgene, cadmium(II) chloride, or zinc(II) chloride to give a C-alkylated aniline.[138] In much the same way N-chloro-N-phenylacetamide (134), when treated with hydrochloric acid, affords N-(4-chlorophenyl)acetamide (135) by a process known as the Orton rearrangement (Scheme 38).[139–142] However, in this case there is evidence that when N-chloro- or N-bromobenzamides are exposed to an acid in an aprotic solvent the corresponding 4-halobenzamides are produced by an intramolecular mechanism that utilizes ion pairs.[143]
Meeeee 88 Meeeeeeee ee 8-Meeeeeeeeeeeeeeee ee eee Meeee Meeeeeeeeeeee[888,888]
Meee 8-eeeeeeeeeeeeeeeee M-(8-eeeeeeeeeeee)eeeeeeeee ee eeeeeee eeee M-eeeeeeeeeeeeeeee ee eee eeeeee eeeeeeeeeeeee, eeeeeee ee eeeeeee eeeee, eeee M-(8-eeeee-8-eeeeeeeeeeee)eeeeeeeee ee eeeeeeee, eee eeee eeeeeeeeeee eeeeeeee eeee eee eeeeeeee eeeeeeee ee Meeee-eeee eeeeeeeeeeeee eeeeee eeeee eeeee eeeeeee eeeeeeeeee.[888]
References
| [138] | Meeeeeee, M. M.; Meeee, M. M.; Meeeeeeee, M.; Meeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [139] | Meeee, M. M., Meeeeeee Meeeeeeeeeeeee, Meeeeeee: Meeeeeeee, (8888); ee 888–888. |
| [140] | Meeeeee, M.; Meeeeeee, M., Me Meeeeeeeeeeee Meeeeee Meeeeeeee, Meeee, M. M.; Meeeeee, M., Mee., Meeeeeee: Meeeee, (8888); Mee. 8, e 888. |
| [141] | Meeee, M. M., Meeeeeee Meeeeeeeeeeeee, Meeeeeee: Meeeeeeee, (8888); ee 888–888. |
| [142] | Meeeee, M. M.; Meeee, M. M., Me Mee Meeeeeeee ee Meeeee, Meeeeee, M., Me.; Meeeeeeeeeee: Mee Meee, (8888); ee 888–888. |
| [143] | Meeeeee, M. M.; Meeee, M.; Meeee, M. M. M.; Meeee, M. M.; Meeeee, M. M., Mee. M. Meee., (8888) 88, 888. |
| [144] | Meeee, M.; Meee, M., Meeee. Meeeee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
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