FLUORINATION WITH CAESIUM FLUOROXYSULPHATE. PART XI. MILD FUNCTIONALIZATION OF SATURATED HYDROCARBONS

Article abstract of DOI:10.1016/S0040-4020(01)80103-4

Several hydrocarbons reacted with caesium fluoroxysulphate in acetonitrile at 35 deg C yielding mono and disubstituted products.Fluorocyclohexane, fluorocycloheptane, and 2-exo-fluoronorbornane formed in the reactions with the corresponding hydrocarbons were accompanied by up to 15percent of other unidentified fluoro products, but their amount was strongly diminished when fluoronation was performed in the presence of nitrobenzene.Fluorination of adamantane resulted in 1-fluoro, 2-fluoro, and 1,3-difluoro substituted products, with the substitution at the tertiary carbon atom strongly predominating.The presence of nitrobenzene did not influence the rate of reaction and the product distribution when the reaction was carried out in acetonitrile, while the introduction of methanol or methanol and nitrobenzene into the reaction mixture slowed down the reaction, with no evidence of the presence of methoxy derivatives.