Boron trifluoride → 1-Acetoxy-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

HRID 1781117Notes

Reaction equation

HRID 1781117 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[C:6]([O:9][N+:10]12[CH2:17][CH2:16][N:13]([CH2:14][CH2:15]1)[CH2:12][CH2:11]2)(=[O:8])[CH3:7].B(F)(F)[F:19].FF>C(#N)C>[F:1][B-:2]([F:5])([F:4])[F:3].[F:1][B-:2]([F:5])([F:4])[F:3].[C:6]([O:9][N+:10]12[CH2:17][CH2:16][N+:13]([F:19])([CH2:12][CH2:11]1)[CH2:14][CH2:15]2)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 24524FluorineHCID 190480361-Acetoxy-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate

Product 1

HCID 190480451-Acetoxy-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-acetoxy-4-aza-1-azoniabicyclo[2.2.2]octane tetrafluoroborate (25.8 g, 10 mmole) and boron trifluoride gas (6.7 g, 10 mmole) in acetonitrile (125 mL) was cooled to 8° C. and treated with a mixture of fluorine in nitrogen (10% V/V, 12 mmole). The reaction was evaporated, the remaining solid washed with dimethoxyethane and dried to afford 1-acetoxy-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate).

Workup

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

Sources & evidence

ORD record
ord-ab4216995e4549fa8ff7ec48a60a94aa
Source dataset
uspto-grants-1997_05
Patent number
US05631372

Reaction notes

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