Quinoline, 2-methyl-*, fluorination

The trichloromethyl group in 4-chIoro-8-methyl-2-(trichloromethyl)quinoline is completely fluorinated with antimony(V) fluoride/antimony(V) chloride when the reaction is carried out in dichloromethane at — 5 to 0 C and then at room temperature for 48 hours to give 4-chloro-8-methyI-2-(trifluoromethyI)quinoIine in 68% yield.4,3... 

R = naphthalene, quinoline, or pyridine, have allowed examination of the inductive effect on electron transfer reactivity. Where the substituent R is methyl or a fluorinated methyl derivative, estimated precursor association constants vary little and thus provide a direct comparison A linear dependence of et on the Taft CT inductive parameter was found for acetato and formato complexes. Although redox potentials for these systems are not readily available, it is thought that they may be correlated with the inductive parameter. Thus —CF3, the most electron-withdrawing of the groups, increases the potential most. 

Reactions, not being accompanied by the displacement of fluorine atoms are also important for functionalization of fluorinated quinolines. For instance, 6-substituted 5,7,8-trifluoroquinolines 148-153 were obtained from 6-trifluoro-methyl-5,7,8-trifluoroquinoline 147 (Scheme 67) through hydrolysis of the CF3 group in quinoline 147 followed by decarboxylation of 5,7,8-trifluoroquinoline-6-carboxylic acid 148 on heating in DMF [6]. From the acid 148 obtained is the acyl chloride 150, which gives with methanol the methyl ester 151 and with ammonia - the amide of... 

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