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

HRID 2210640Notes

Reaction equation

HRID 2210640 reaction equation
[N:1]12[CH2:8][CH2:7][N+:4]([O-:9])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[F:10][B-:11]([F:14])([F:13])[F:12].[Na+].[F:16]F>C(#N)C>[F:10][B-:11]([F:14])([F:13])[F:12].[F:10][B-:11]([F:14])([F:13])[F:12].[OH:9][N+:4]12[CH2:7][CH2:8][N+:1]([F:16])([CH2:6][CH2:5]1)[CH2:2][CH2:3]2

Participants

5

Reactant 3

HCID 24524FluorineHCID 4343483Sodium TetrafluoroborateHCID 111371811,4-Diazabicyclo(2.2.2)octane, 1-oxide

Product 1

HCID 27373291-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)Yield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,4-diazabicyclo[2.2.2]octane N-oxide (1.26 g, 9.8 mmole) and sodium tetrafluoroborate (1 g, 9.1 mmole) in acetonitrile (250 mL) was cooled to 8° C. and treated with a mixture of fluorine in nitrogen (10% V/V, 30 mmole). The reaction was evaporated, the remaining solid washed with acetone and dried to afford 1.03 grams of 1-hydroxyl-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (70% yield).

Workup

  1. customThe reaction was evaporated
  2. washthe remaining solid washed with acetone
  3. customdried

Sources & evidence

ORD record
ord-8339b4011aa94366b38ff084e223e8e7
Source dataset
uspto-grants-1995_10
Patent number
US05459267

Reaction notes

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