Compound 2b

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Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

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

A mixture of 1b (523 mg, 0.50 mmol) and NO·SbF₆ (159 mg, 0.60 mmol) in DCM (10 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 toluene (3 x 5 mL), and dried in vacuo at 140 °C overnight, to afford 2b as an off-white solid (352 mg, 275 mmol, 55% yield). ¹H NMR (300 MHz, CDCl₃) δ 9.10 (s, 2H), 7.75–7.67 (m, 6H), 7.47 (dd, J = 5.8, 3.2 Hz, 2H), 7.39 – 7.21 (m, 48H); ¹³C NMR (126 MHz, CDCl₃) δ 169.0 (1C, N=CH₂), 143.7 (8C, 4°), 139.8 (2C, 4°), 139.5 (8C, 4°), 138.0 (4C, 4°), 131.4 (2C, 3°), 129.1 (16C, 3°), 128.6 (4C, 3°), 128.3 (8C, 3°), 127.4 (16C, 3°), 126.3 (2C, 3°), 126.1 (8C, 3°), 90.0 (2C, 4°); ¹⁹F NMR (471 MHz, CDCl₃) δ –121.7 (br m); HRMS (m/z): [M]⁺ calcd. for C₈₁H₅₈N, 1044.4564; found, 1044.4556.