Compound 2c

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Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

Compound data: IR

Compound data: Crystallographic data

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

A mixture of 1c (1.07 g, 0.50 mmol) and NO·SbF₆ (160 mg, 0.60 mmol) in acetonitrile (15 mL) was stirred at room temperature for 3 hours. The resulting solution was filtered through a cannula equipped with a glass filter, and evaporated to dryness. Then, the obtained solid was thoroughly dried in vacuo at 140 °C overnight. After cooling to room temperature, the solid residue was washed with a minimum amount of DCM, and dried in vacuo at 140 °C overnight, to afford 2c as an orange solid (1.15 g, 0.49 mmol, 98% yield). Recrystallization from hot 1,1,2,2-tetrachloroethane solution afforded single crystals suitable for X-ray crystallographic analysis. ¹H NMR (300 MHz, CDCl₃) δ 9.42 (s, 2H), 7.94 (dd, J = 5.9, 3.1 Hz, 2H), 7.73 (s, 8H), 7.67 (s, 4H), 7.66–7.58 (s, 16H), 7.53 (dd, J = 5.9, 3.1 Hz, 2H), 7.43–7.31 (s, 8H); ¹³C NMR (201 MHz, CH₃CN) δ 172.3 (1C, N=CH₂), 141.8 (8C, 4°), 140.9 (8C, 4°), 140.0 (4C, 4°), 139.4 (2C, 4°), 132.7 (2C, 3°), 132.4 (q, ²J_C-F = 33.4 Hz, 16C, 4°), 129.5 (4C, 3°), 129.2 (8C, 3°), 128.7 (16C, 3°), 127.4 (2C, 3°), 124.2 (q, ¹J_C-F = 272.4 Hz, 16C, 4°), 122.9 (8C, 3°), 89.6 (2C, 4°); ¹⁹F NMR (471 MHz, CDCl₃) δ −63.2, −119.8 (br); HRMS (m/z): [M]⁺ calcd. for C₉₇H₄₂F₄₈N, 2132.2545; found, 2132.2557.