Hydrogen Peroxide → 1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Reaction equation
[N:1]12[CH2:8][CH2:7][N:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.OO.B(F)(F)[F:12].[F:15][B-:16]([F:19])([F:18])[F:17].[H+].FF.[OH2:23]>>[F:15][B-:16]([F:19])([F:18])[F:17].[F:15][B-:16]([F:19])([F:18])[F:17].[OH:23][N+:1]12[CH2:8][CH2:7][N+:4]([F:12])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2Participants
7
Conditions
- Temperature
- 20 °C
Procedure
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 15°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).
Workup
- temperaturethe solution cooled to 9° C.
- customThe reaction was evaporated
- washthe remaining solid washed with acetone
- customdried
Sources & evidence
- ORD record
- ord-26dedc844817457ea006039257759cb3
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05606084
Reaction notes
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