Evans, G., Gibbs, T.J.K., Jenkins, R.L., Coles, S.J., Hursthouse, M.B., Platts, J.A. and Tomkinson, N.C.O. (2008) Kinetics of iminium ion catalysis. Angewandte Chemie International Edition, 47 (15), 2820-2823. (doi:10.1002/anie.200705539).
Abstract
To a stirred solution of cinnamaldehyde (118 mg, 1.42 mmol, 122 ?l) in methanol (2ml), trifluoromethylpyrrolidine (198 mg, 1.42 mmol) was added and allowed to stir at ambient temperature for 2 minutes. After this time, hexafluorophosphoric solution in H2O (60% w/w) (345 mg, 1.42 mmol, 210 ?l) was added which immediately formed a yellow precipitate on addition. The excess solvent was removed in vacuo and the crude mixture was recrystallised from hot methanol to give 6 (493 mg, 87%) as an off white solid; mp 199-201 oC; ?max(Nujol) 2923, 2853, 1621, 1591, 1456, 1376 cm-1; 1H NMR (400MHz, CD3CN) ? 8.64 (d, J = 10.6 Hz, 1H), 8.12 (d, J = 15.2 Hz, 1H), 7.91-7.89 (m, 2H), 7.69-7.67 (m, 1H), 7.60-7.57 (m, 2H), 7.32 (dd, J = 10.6Hz, 15.2Hz, 1H), 5.0-4.96 (m, 1H), 4.24-4.14 (m, 2H), 2.52-2.45 (m, 1H), 2.42-2.27 (m, 3H); 13C NMR (125 MHz, CDCl3) ? 170.8, 165.3, 134.9, 131.2, 129.7, 125.1, 118.4, 66.8 (q, J1CF = 31.3 Hz), 53.3, 24.9, 22.6, 21.7; m/z (APCI) 254 [M–PF6]?+; HRMS (ES) found 254.1152 [M–PF6].+; calculated for C14H15NF3 254.1151.
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