122180-10-3Relevant articles and documents
N-HALOGENO-COMPOUNDS. PART 10. N-FLUOROQUINUCLIDINIUM TRIFLATE
Banks, Ronald Eric,Sharif, Iqbal
, p. 297 - 300 (1988)
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.
N-Halogeno compounds. Part 13. N-Fluoroquinuclidinium salts - synthesis and use as electrophilic fluorinating agents
Banks, Ronald Eric,Sharif Iqbal
, p. 207 - 214 (1991)
A convenient one-pot method has been developed for the preparation of the easily handled electrophilic fluorinating agent N-fluoroquinuclidinium triflate from quinuclidine, lithium triflate and fluorine.The corresponding trifluoroacetate, heptafluoro-n-butyrate and tetrafluoroborate salts were procured in a two-step fashion by adding the appropriate sodium salts to acetonitrile solutions of N-fluoroquinuclidinium fluoride.Site-specific fluorination of phenylmagnesium bromide (to PhF), diethyl sodio(phenyl)malonate , 2-nitropropan-2-yl-lithium , 1-morpholinocyclohexene >, phenol (to 2- and 4-FC6H4OH + 1,4-F2C6H3OH) and sodium benzenesulphinate (to PhSO2F) was achieved using these new N-fluoroquinuclidinium salts.