Quinoline, heptafluoro

VI.—Simple In compounds with bidentate monoprotic organic ligands have been reported for the first time, i.e. InX [X = 4,4,4-trifluoro-l-(thien-2 -yl)butane-l,3-dionate, 6, 6, 7, 7, 8, 8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-dionate, quinolin-... 

Heterocycles containing limited amount of fluorinated substituents (usually 1-3) can be named using trivial names or conventional nomenclature in combination with indication of the position of fluorinated substituents, for example, 2-fluoro-4-tri-fluoromethylpyridine. The situation becomes more complicated in case of poly-fluorinated and completely fluorinated heterocycles. In case of heterocycles with relatively small number of fluorinated substituents and well-defined stmctures, Greek or Latin numeral roots can be used. Names such as hexafluoropropene oxide, 2,2-bis (trifluoromethyl)oxirane, 2,2,3,3-tetrafluorooxetane, tetrakis(trifluoromethyl)furane, pentafluoropyridine, tetrafluoropyridazine, tetrafluoropyrimidine, and heptafluoro-quinoline are unambiguous and commonly accepted (see Fig. 0.1). 

When pentafluoropyridine and heptafluoro-quinoline and -isoquinoline react with hydrogen diloride or bromide in suipholane, replacement of fluorine ortho and para to the nitrogen by halogen occurs. The order of reactivity is heptafluoroquinoline > heptafluoroisoquinoline > pentafluoropyridine traces of water lead to a considerable rediKtion in the reaction rate and to the formation of hydroxy-daivatives. The proposed mechanism for these reactions, involving nucleophilic displacement of fluoride ion from the protonated heterocycle, is illustrated for heptafluoroquinoline in Scheme 52. No evidence for initial attack at the 4-position was obtained, mid 2,4-dichloro-pentafluoroquinoline was obtained in high yield. 

Brooke G, Chambers R, Drury C, Bower M (1993) Remarkable orientationeil effects in the displacement of the fluorine from heptafluoro-isoquinoline and -quinoline towards sitlfur nucleophiles. Further reactions with oxygen nucleophiles. J Chem Soc, Perkin Trans I 1993 2201-2209... 

Chambers RD, Hole M, Iddon B, Musgrave WKR, Storey RA (1966) PolyfluoroheterocycUc compounds. Part VII. Heptafluoro-quinoline and -isoquinoline. J Chem Soc C 2328-2331... 

Chambers RD, Hole M, Musgrave WKR, Thorpe JG (1971) Polyfluoroheterocyclic compounds. Part XVIII. Reactions of heptafluoro-quinoline and -isoquinoline and pentafluoro-pyridine with hydrogen halides. J Chem Soc C 61-67... 

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