Quinuclidine → HCID 15252126, compound

Participants

Reaction Steps

Using the apparatus and techniques previously employed to convert quinuclidine to N-fluoroquinuclidinium triflate in a closed reactor (R. E. Banks et al, J. Chem. Soc., Perkin Trans. I, 1988, 2805 and R. E. Banks and I. Sharif, J. Fluorine Chem., 1988, 41, 297) a degassed solution of 1-methyl-4-aza-1-azoniabicyclo[2,2,2]octane triflate (2.18 g, 7.90 mmol) and lithium triflate (1.23 g, 7.90 mmol) in cold (-35° C.), dry acetonitrile (200 cm3), was treated with neat fluorine (less than 20 mmHg (2.7 kPa) pressure) until absorption of the fluorine became imperceptible (3 hours). The reaction mixture was allowed to warm to room temperature, filtered to remove lithium fluoride which had precipitated, and the filtrate rotary evaporated and recrystallized from methanol to give 1-fluoro-4-methyl-1,4-diazoniabicyclo [2,2,2]octane ditriflate (3.10 g, 6.98 mmol, 88%). (Found: C, 24.0; H, 3.6; F, 29.8; N, 6.4%. Calc. C, 24.3; H, 3.4; F, 29.95; N, 6.3%), m.p. 220°-222° C. δF (solution in D2O; ext. CF3CO2H ref.) 1.0 (s; CF3SO3-), 124.5 (br. m; FN+) p.p.m., δH (same solution) 3.44 (s; CH3N+), 4.43 (m; 3×CH2), 4.88 (m; 3×CH2) p.p.m. [residual H in D2O, 4.68 (s) p.p.m⟧

Provenance & Evidence