Polyhalogenated heterocyclic compounds: Part 45. Reactions of perfluoro-(4-isopropylpyridine) with oxygen, nitrogen and carbon nucleophiles

Reactions between perfluoro-(4-isopropylpyridine) (1) and a variety of oxygen-, nitrogen- and carbon-centred nucleophiles are reported. A range of mono-, di- and tri-substituted perfluoro-(4-isopropylpyridine) derivatives were synthesised for which yields and regiochemistry depended on reaction conditions. The barriers to rotation for the perfluoro-isopropyl group in several pyridine systems were measured by 19F NMR spin-saturation transfer experiments.