Polyhalogenoaromatic compounds. Part 53. Substitution in polyfluoroaromatic compounds by bulky nucleophiles

Abstract

Potassium t-butoxide in THF is highly reactive towards polyfluoroaromatic compounds. The position(s) of substitution are generally similar to those observed with other nucleophiles, though octafluoronaphthalene undergoes ca. 30% 2,7-disubstitution. Hexafluorobenzene, octafluoronaphthalene, pentafluoropyridine, and 3,5-dichlorotrifluoropyridine also undergo substitution by lithium di-isopropylamide; in the last case substitution occurs in the 2-position.