MILD OXIDATION OF ALKYL-HALIDES

The application of N-phenyltrifluoromethanesulfonamide to the oxidation of activated halides (α-halo carbonyl compounds) has been extended and shown to be general. A new reagent, N-(4-acetoxyphenyl)trifluoromethanesul-fonamide, has been developed for the mild oxidation of unactivated alkyl halides. The reagent was N-alkylated with a number of different alkyl halides. The elements of CF3SO2H were then eliminated under mild basic conditions generating imines which were easily hydrolyzed to the corresponding amines and carbonyl compounds. The ease of CF3SO2-elimination was demonstrated to be dependent on intermediate aminoquinone formation. © 1979, American Chemical Society. All rights reserved.