Syntheses of heterocyclic compounds. Part XIX. Preparation and nucleophilic reactions of polyhalogeno-substituted N-oxides

Abstract

The preparation and reactions of various polyfluorophenyl-substituted N-oxides with secondary and primary amines are described. The former give predominantly di-ortho- and the latter mono-o-substituted products. p-Substitution prevails, however, with methanol or water as solvent. Structural assignment of the products was made on the basis of their ¹⁹F nuclear magnetic resonance spectra and a mechanism to account for the orientation is discussed.