Trifluoroacetamides
T. W. Green, P. G. M. Wuts,
Protective Groups in Organic
Synthesis,
Wiley-Interscience, New York, 1999, 604-607, 744-747.
Stability
| H2O: | pH < 1, 100°C | pH = 1, RT | pH = 4, RT | pH = 9, RT | pH = 12, RT | pH > 12, 100°C |
| Bases: | LDA | NEt3, Py | t-BuOK | Others: | DCC | SOCl2 |
| Nucleophiles: | RLi | RMgX | RCuLi | Enolates | NH3, RNH2 | NaOCH3 |
| Electrophiles: | RCOCl | RCHO | CH3I | Others: | :CCl2 | Bu3SnH |
| Reduction: | H2 / Ni | H2 / Rh | Zn / HCl | Na / NH3 | LiAlH4 | NaBH4 |
| Oxidation: | KMnO4 | OsO4 | CrO3 / Py | RCOOOH | I2, Br2, Cl2 | MnO2 / CH2Cl2 |
Other Syntheses of Triflouroacetylated Amino Groups
A mild deprotection for notoriously difficult to unmask primary N-(p-toluenesulfonyl)
amides occurs at low temperature by initial activation of the nitrogen with a
trifluoroacetyl group, followed by reductive cleavage of the p-toluenesulfonyl
group with samarium diiodide.
Z. Moussa, D. Romo, Synlett, 2006,
3294-3298.
