When treated with tert-butyllithium in THF at -50 Deg, N-BOC (tert-butoxycarbonyl) protected fluoroanilines and trifluoromethylanilines, e.g., o-, m-, or p-F3CC6H4NHCO2CMe3, undergo metalation at the position adjacent to that carrying the nitrogen. If, however, the nitrogen carries two alkyl or trimethylsilyl groups as substituents and highly polar metalating reagents such as butyllithium activated by N,N,N',N\",N\"-pentamethyldiethylenetriamine (PMDTA) or potassium tert-butoxide are employed, the fluoroaniline derivs. are preferentially deprotonated next to the halogen atom. [on SciFinder (R)]
Titre
Fluorine and trifluoromethyl substituted anilines: site selective metalation and electrophilic substitution
Publié dans
Synlett
Numéro
4
Pages
360-362
Date
1992
ISSN
0936-5214
Note
CAN 117:7608
25-17
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
403-46-3; 60144-53-8; 81740-18-3; 98968-72-0; 109134-07-8; 141940-36-5; 141940-37-6; 141940-38-7; 141940-39-8 Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation of, regioselectivity in); 446-31-1P; 141940-27-4P; 141940-28-5P; 141940-29-6P; 141940-30-9P; 141940-31-0P; 141940-32-1P; 141940-33-2P; 141940-34-3P; 141940-35-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Date de création de la notice
2006-03-03