Fluorinations with potassium tetrafluorocobaltate(III). Part VI. Fluorination of pyridine and 4-methylpyridine

Abstract

Pyridine has been fluorinated over KCo^IIIF₄ to give a mixture largely of ring-opened products. The main components isolated were (Z)-undecafluoro-2-azahex-2-ene (I), (Z)-2H-1-bistrifluoromethylaminotetrafluoroprop-1-ene (II), (E)-2H-1-bistrifluoromethylaminotetrafluoroprop-1-ene (III), (Z)-5H-decafluoro-2-azahex-2-ene (IV), (2Z,4E)-4H,5H-heptafluoro-2-azahexa-2,4-diene (V), (2Z,4Z)-5H-octafluoro-2-azahexa-2,4-diene (VI), (2Z,4E)-5-bistrifluoromethylamino-octafluoro-2-azahexa-2,4-diene (VII), (2Z,4Z)-5-bistrifluoromethylamino-octafluoro-2-azahexa-2,4-diene (VIII), and 3H-1-difluoromethylheptafluoropyrrolidine(IX). In a similar manner, fluorination of 4-methylpyridine gave the analogous compounds (Z)-5-trifluoromethyldecafluoro-2-azahex-2-ene (X), (Z)-5-trifluoromethyloctafluoro-2-azahexa-2,4-diene (XI), (Z)-5-methyldecafluoro-2-azahex-2-ene (XII), and (Z)-5-difluoromethyldecafluoro-2-azahex-2-ene (XIII) as major components.