Reduction carbon-fluonne bond

The carbon-oxygen bond is strong, like the normal carbon-fluonne bond, it is difficult to reduce However, some structural features facditate its reductive cleavage Aiyl esters of perfluoroalkanesulfomc acids can be cleaved in good yield by... 

Electrochemical reduction of carbon-fliionne bonds occurs at high pH when a carbonyl group is adjacent Polaiographic reduction of a a,a-tnfluoroacetophe-none without loss of fluonne predominates in acidic media to give the alcohol and the corresponding pinacol, whereas reduction of the unprotonated ketone results in hydrogenolysis of the tnfluoromethyl group to form acetophenone as product Il] (equation 8)... 

Reductive removal of fluonne from alky I fluorides requires a potent reducing agent and so is not normally encountered However, hydrogenolysis of an unactivated carbon-fluorine bond in, for example, 3 p-fluorocholestane has been efficiently accomplished in 88% yield with a solution of potassium and dicyclohexyl 18 crown-6 in toluene at 25 °C [/] Similarly, sodium naphthaiene in tetrahydrofuran converts 6 fluorohexene-1 and 1-fluorohexane to hydrocarbons in 50% yield at 25 °C over a 7-h period [2]... 

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