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

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,4-diazabicyclo[2.2.2]octane (11.2 g, 0.1 mole) in water (100 mL) was added 30% hydrogen peroxide (22.8 mL) while maintaining the temperature between 1-5 and 20° C. The reaction was stirred at room temperature (20°-22° C.) overnight. Next, boron trifluoride gas (6.8 g, 0.1 mole) and tetrafluoroboric acid (50% solution, 10 mL, 0.1 mole) were added, the solution cooled to 9° C. and treated with a mixture of fluorine in nitrogen (10%V/V, 0.125 mole). The reaction was evaporated, the remaining solid washed with acetone and dried to afford 30 grams of 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (93% yield).

Provenance & Evidence