Trifluoromethanesulfonic acid, lithium salt → HCID 10742526, compound

HRID 1534076Notes

Reaction equation

HRID 1534076 reaction equation
[O-:1][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[CH2:9]([N+:11]12[CH2:18][CH2:17][N:14]([CH2:15][CH2:16]1)[CH2:13][CH2:12]2)[CH3:10].[O-:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21].[Li+]>C(#N)C>[O-:4][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:3])=[O:1].[O-:22][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:21])=[O:19].[CH2:9]([N+:11]12[CH2:18][CH2:17][N+:14]([F:24])([CH2:15][CH2:16]1)[CH2:13][CH2:12]2)[CH3:10]

Participants

4

Reactant 2

HCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 15252136HCID 15252136, compound

Product 1

HCID 10742526HCID 10742526, compoundYield 159.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction described in Example ID was repeated, using 1-ethyl-4-aza-1-azoniabicyclo[2,2,2]octane triflate (1.5 g, 5.2 mmol) in dry acetonitrile (200 cm3) in place of its N-methyl analogue and an equimolar proportion of lithium triflate (0.8 g). Work-up of the product, as in Example ID, afforded 1-ethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane ditriflate (1.9 g, 4.1 mmol, 80%), m.p. 236°-238° C. (dec.), δF (soln. in D2O; ext. TFA) 0.02 (s; CF3SO3-), 124.0 (br. m; FN+) p.p.m., δH (same soln.) 1.48 (t: CH3), 3.79 (q; CH2CH3), 4.40 (m: 3×ring CH2), 4.95 (m; 3 ring CH2) p.p.m. [residual H in D2O, 4.78 (s) p.p.m⟧

Sources & evidence

ORD record
ord-9a3cc82ced94490bb126f9aaa5f9954b
Source dataset
uspto-grants-1992_02
Patent number
US05086178

Reaction notes

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