Compound 8

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Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

Compound data: Crystallographic data

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

In a 15-mL scintillation vial, a mixture of 2c (47.3 mg, 20 µmol) and cyclohexene (100 mg, 1.2 mmol, distilled from calcium hydride and stored over 3Å molecular sieves) was chilled for 1 hour in a glovebox coldwell cooled with dry ice/acetone bath. Then, a pre-cooled solution of KHMDS (6.0 mg, 30 µmol) in MTBE (2.0 mL) was added, and the mixture was stirred with cooling for 30 minutes. Then, the resulting mixture was passed through a glass filter, evaporated to dryness, recrystallized from chloroform/hexane (vapour diffusion) at room temperature, to afford 8 as colourless crystals suitable for X-ray crystallographic analysis. The crystals were grounded and dried in vacuo at 120 °C overnight to afford 8 as a colourless powder (40.7 mg, 18 µmol, 92% yield). ¹H NMR (300 MHz, CDCl₃) δ 7.81 (s, 8H), 7.73 (s, 16H), 7.70 (s, 4H), 7.61 (s, 8H), 7.43–7.36 (m, 2H), 7.25–7.20 (m, 2H), 2.31 (NCH, br s, 1H), 1.50–0.69 (m, 10H); ¹³C NMR (201 MHz, CDCl₃) δ147.1 (4C, 4°), 144.3 (2C, 4°), 141.7 (8C, 4°), 139.2 (8C, 4°), 132.5 (q, ²J_C-F = 33.7 Hz, 16C, 4°), 129.4 (2C, 3°), 128.8 (8C, 3°), 126.8 (16C, 3°), 125.4 (4C, 3°), 124.8 (2C, 3°), 123.1 (q, ¹J_C-F = 273 Hz, 16C, 4°), 122.0 (8C, 3°), 81.7 (2C, 4°), 40.1 (1C, NCHR₂), 23.4 (2C, 2°), 21.3 (2C, 2°), 19.5 (2C, 3°); ¹⁹F NMR (282 MHz, CDCl₃) δ −63.1; HRMS (m/z): [M+TFA−H]⁻ calcd. for C₁₀₃H₅₁F₄₈N·CF₃CO₂, 2326.3111; found, 2326.3102.