Abstract
The carbon-fluorine bond, noted for its strength1, has been of chemical interest2 even before Moissan's discovery of elemental fluorine. The most electronegative element, fluorine is uniquely capable of replacing all the hydrogen atoms in every hydrocarbon system3, yielding materials such as polytetrafluoroethylene renowned for their combination of rare physical properties, out-standing chemical inertness and high thermal stability4, with sig-nificant modern technological applications5,6. Reaction of satur-ated fluorocarbons requires extreme conditions1, for example treat-ment with metals at ∼500 °C7 or high-energy irradiation8. Following an observation by MacNicol and McGregor (unpublished data) of an unprecedented reactivity under mild conditions we now report specifically the efficient transformation of perfluorodecalin (1) to known host molecules by arenethiolate nucleophiles in dipolar aprotic solvent. This chemistry is not only of fundamental mechanistic interest, but also creates new synthetic possibilities in various fields. For example, preparing novel hosts for inclusion chemistry9, a subject attracting much current attention.
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MacNicol, D., Robertson, C. New and unexpected reactivity of saturated fluorocarbons. Nature 332, 59–61 (1988). https://doi.org/10.1038/332059a0
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DOI: https://doi.org/10.1038/332059a0
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