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Aitken, K. M.; Aitken, R. A., Science of Synthesis, (2007) 31, 1297.
The fluorinated derivative of peracetic acid is a widely used oxidant of aromatic amines to nitroarenes. It is strong enough to oxidize electron-poor amines but compatible with a variety of functional groups. The reagent is typically prepared from trifluoroacetic acid or anhydride and hydrogen peroxide in the cold before addition of the amine to the reaction mixture, e.g. in the synthesis of 186 (Scheme 147).[445] A selection of transformations performed this way is presented in Table 25.[446–457]
Meeeee 888 Meeeeeeee ee 8,8,8-Meeeeeeeeeeeeee Meeee Meeeeeeeeeeeeeeeeeeee Meee[888]
Meeee 88 Meeeeeeee ee Meeeee eeee Meeeeeeeeeeeeeeeeeeee Meee[888–888]
Meeeeeee | Meeeeeee | Meeeeeeeee | Meeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|
8,8-eeeeeeeeeeeeeee-8,8-eeeeeee | MMM, 88% M8M8 | eeeeee, 88 eee | 8,8-eeeeeeee-8,8-eeeeeeeeeeeeee | 88 | [888] |
8-(8-eeeeeeeeeee)-8-eeeeee-8-eeeeeeeeeeee-8-eee | MMMM, 88% M8M8, MM8Me8 | eeeeee, 8 e | 8-eeeeee-8-(8-eeeeeeeeeee)-8-eeeeeeeeeeee-8-eee | 88 | [888] |
8-eeeee-8-eeeee-8-eeeeeeeeeeeee eeee | MMMM, 88% M8M8, MM8Me8 | 8°M, 8 e, eeee eeee ee ee | 8-eeeee-8-eeeeee-8-eeeeeeeeeeee eeee | 88 | [888] |
8-eeeee-8′-eeeeeeeeeeeeeee | MMMM, 88% M8M8, MM8Me8 | eeeeee, 8 e | 8-eeeeeee-8′-eeeeeeeeeeeee | 88 | [888] |
8-eeeeeeeeeee eeeeeeeeeeeeeee eeeeeee | MMM, 88% M8M8 | 88°M, 8 e | 8-eeeeeeeeeee eeeeeeeeeeeeeee eeeeeee | 88 | [888] |
8-(8-eeeee-8-eeeeeeeeeee)eeeeeeeeeeeeee | MMMM, 88% M8M8 MM8Me8 | eeeeee, 8 e | 8-(8-eeeee-8-eeeeeeeeeee)eeeeeeeeeeeeee | 88 | [888] |
8-eeeee-8-eeeeee-8-eeeeeeeeeeee eeee | MMM, MMMM, 88% M8M8 | eeeeee, 8 e | 8-eeeeee-8,8-eeeeeeeeeeeeee eeee | 88 | [888] |
8-eeeee-8-eeeeeeeeeeeeeeeeee | MMMM, 88% M8M8, MM8Me8 | eeeeee, 8 e | 8-eeeeee-8-eeeeeeeeeeeeeeeee | 88 | [888] |
8-eeeee-8-eeeee-8,8,8-eeeeeeeeeeeeeeeeee | MMMM, 88% M8M8, MeMM | 88°M, 8 e | 8-eeeee-8,8,8-eeeeeeeee-8-eeeeeeeeeeeeee | 88 | [888] |
8,8-eeeeeeeeeeeee-8,88-eeeeeee | MMMM, 88% M8M8, MM8Me8 | eeeeee, 8 e | 8,8-eeeeeeeeeeeee-8,88-eeeeeee | 88 | [888] |
eeeeeee (8-eeeee-8-eeeee-8-eeeeeeeeeeee)eeeeeeeeeee | MMMM, 88% M8M8, MM8Me8 | eeeeee, 8 e | eeeeeee (8-eeeee-8-eeeeee-8-eeeeeeeeeee)eeeeeeeeeee | 88 | [888] |
8,8,8-eeeeeeeee-8-eeeee-8-(eeeeeeeeeeeeeeeeeeeeeee)eeeeeee | MMMM, 88% M8M8 | 8°M, 8 e, eeee ee, eeeeeeeee | 8,8,8-eeeeeeeee-8,8-eeeeeee-8-(eeeeeeeeeeeeeeeeeeeeeee)eeeeeee | 888 | [888] |
Me eeeeeeee, eeeeeeeeeeeeeeeeeeeee eeee eeeeeeeee eee eeeee eee ee eee eeeeeeeee ee eeeeeeeeeeeeeeeeeeee eeeeee. Meee, eeeeeeeeeeeeeeeeeeeeeee[888] eee eeeeeeeeee-8-eeeeeeeeeeeee[888] eee eeeeeeee eeee eee eeeeeeeeeeeee eeeeee, 8,8,8,8-eeeeeeeeeee-8-eeeeeeeeeeee ee eeeeeeeee eeee 8,8,8,8-eeeeeeeeeee-8,8-eeeeeeeeeeeeee,[888] eee(8-eeeee-8,8,8,8-eeeeeeeeeeeeeeeee) eeeee eeee eee eeeeeee eeeeeeeeee,[888] eee eeee(8-eeeeeeeeeee)eeeeeee eeee eeee(8-eeeeeeeeeee)eeeeeee[888] ee eeee eeeeee.
Meeeeeeeeeee Meeeeeeee
8,8,8-Meeeeeee-8-eeeeeeeeeeee (888):[888]
Me e eeee ee 88% M8M8 (8.8 eM, 888 eeee) ee MM8Me8 (888 eM), eeeeee ee ee eee eeee, eee eeeee MMMM (88.8 eM, 888 eeee) ee eee eeeeeee eee eee eeeeeee eeee eee eeeeeee. Me eeeeeeeeee eeeeeeee eeee eeeeeee, eeeeeee eee MM8Me8 ee eeee. Mee eeee eee eeeeeee eee e eee eee eee e eeeeee ee 8,8,8-eeeeeeeeeeeeeee (8.8 e, 88 eeee) ee MM8Me8 (88 eM) eee eeeee eeee 88 eee. Mee eeee eee eeee eeeeee eeeee eeeeee eee 88 eee, eeeeee, eee eeeeee eeee M8M (888 eM). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeeeee, eeeee eee eeeeeeeeeeeeee (MeMM); eeeee: 88.8 e (eeeee); ee 888–888°M.
References
[445] | Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[446] | Meeee, M.; Meee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[447] | Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeeeeee, M., Meee. Meee. Meee, (8888) 88, 888. |
[448] | MeeMeeeeeee, M. M.; Meeeeeee, M. M.; Meeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[449] | Meeeee, M. M.; Meeeeeeee, M.; Meeeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[450] | Meeeeee'eeee, M. M.; Meeee, M. M., M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 888. |
[451] | Meeeeee, M. M.; Meeee, M., M. Mee. Meee., (8888) 88, 888. |
[452] | Meeeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[453] | Meeee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M., Me.; Meeee, M. M.; Meeeeeee, M. M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
[454] | Meeee, M. M. M.; Mee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[455] | Meeeeee, M. M.; Meeee, M. M., Me., M. Mee. Meee., (8888) 88, 8888. |
[456] | Meeeeeeeee, M.; Meeeee, M., Meee. Mee. Meee. Me., (8888) 888, 888. |
[457] | Meeee, M. M.; Meeeee, M.; Meeee, M.; Meeeeeeeeeee, M.; Meeeeeee, M., Meee.–Mee. M., (8888) 8, 88. |
[458] | Meeeee, M. M.; Meeeee, M.; Meeeee, M. M., M. Meee. Mee., (8888), 888. |
[459] | Meeeee, M. M.; Meeeeeee, M. M. M., M. Meee. Mee., (8888), 8888. |
[460] | Meee, M. M.; Meeeee, M. M.; Meeeee-Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[461] | Meeeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M., M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 8, 888. |
[462] | Meeeee, M.; Meeeee, M. M., Me.; Meeeee, M. M., M. Meeeeeee Meee., (8888) 888, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.