Hydrogen Peroxide → 1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

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Reaction Steps

1,4-Diazabicyclo[2.2.2]octane N-oxide was prepared by the reaction of 1,4-diazabicyclo[2.2.2]octane with hydrogen peroxide as described by Farkas in J. Chem. Eng. Data (1968) 13,278. A solution of 1,4-diazabicyclo[2.2.2]octane N-oxide (1.28 g, 10 mmole), sodium tetrafluoroborate (1.1 g, 10 mmole), and tetrafluoroboric acid (50% solution, 1.83 g, 10 mmole) in acetonitrile (250 mL) was cooled to -35° C. and treated with a mixture of fluorine in nitrogen (10% V/V, 14 mmole). The reaction was evaporated, the remaining solid washed with acetone and dried to afford 1.23 grams of 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate) (38% yield); m.p. 336-8° C.; 1H NMR (D2O): d 5.0 (m, 6H), 4.6 (m, 6H); 13C NMR (D2O): d 61.6 (d, J=15.5 Hz), 62.3 (d, J=6.2 Hz); 19F (D2O): d 41 (1F), -150 (8 F); 15(D2): d -207.5 (d, J=84 Hz), -275.9. Anal. Calcd for C6H13B2F9N2O: C, 22.40; H 4.07; N, 8.70; B, 6.72. Found: C, 22.69; H, 4.25; N, 8.80; B, 6.39.

Provenance & Evidence