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- W2061293048 abstract "Abstract Fluorine smoothly attacks quinuclidine-trifluoroborane, quinuclidine-pentafluorophosphorane, and quinuclidine-sulfur trioxide in acetonitrile at −35 °C to give the corresponding N -fluoroquinuclidinium salts NFQ + X − (X − BF 4 − , PF 6 − , and FSO 3 − respectively; Q = quinuclidine). Like its tetrafluoroborate analogue (NFQ + BF 4 − ), the hexafluorophosphate NFQ + PF 6 − can also prepared by direct fluorination of quinuclidine in the presence of the appropriate sodium salt (NaPF 6 ). An alternative route to the tetrafluoroborate involves treatment of NFQ + F − with boron trifluoride. A comparative study of site-specific electrophilic fluorination of methoxybenzene [ → 1-fluoro-2- and 4-methoxybenzene], 2-hydroxynaphthalene ( → 1-fluoro-2-hydroxynaphthalene and 1,1-difluoro-2-oxo-1,2-dihydronaphthalene), 2-nitropropan-2-yl-lithium ( → 2-fluoro-2-nitropropane) and diethyl sodio(phenyl)malonate [ → diethyl fluoro(phenyl)malonate] with all of the NFQ + X − salts mentioned above, plus the triflate (X − CF 3 SO 3 − ), revealed that the hexafluorophosphate and triflate are the most easily-handled and effective reagents." @default.
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- W2061293048 date "1996-02-01" @default.
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- W2061293048 title "N-Halogeno compounds. Part 15. Synthesis of N-fluoroquinuclidinium salts via direct fluorination of quinuclidine-Lewis acid adducts, and a comparison of their “F+” transfer capabilities" @default.
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- W2061293048 doi "https://doi.org/10.1016/0022-1139(95)03356-4" @default.
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