N-HALOGENO-COMPOUNDS. PART 10. N-FLUOROQUINUCLIDINIUM TRIFLATE

Article abstract of DOI:10.1016/S0022-1139(00)81553-5

Direct fluorination of quinuclidine at ca. -33 deg C in acetonitrile containing lithium trifluoromethanesulphonate (triflate) gives N-fluoroquinuclidinium triflate (2) in excellent yield.Similar fluorination of quinuclidine in trichlorofluoromethane at -78 deg C, followed by treatment of the resultant N-fluoroquinuclidinium fluoride (1) with trimethylsilyl triflate, also yields the new triflate, but in somewhat lower yield (80percent).N-Fluoroquinuclidinium triflate (2) is much more convenient to use as an electrophilic fluorinating agent than the fluoride (1) owing to its non-hygroscopic nature.