Compound 2a

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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 1a (875 mg, 2.0 mmol) and NO·SbF₆ (585 mg, 2.2 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 ether (3 x 10 mL), and dried in vacuo at 140 °C overnight, to afford 2a as an off-white solid (924 mg, 1.37 mmol, 69% yield). ¹H NMR (300 MHz, CDCl₃) δ 8.44 (s, 2H), 7.63 (dd, J = 5.8, 3.2 Hz, 2H), 7.43–7.26 (m, 12H), 7.22 (dd, J = 5.8, 3.2 Hz, 2H), 7.08–6.94 (m, 8H); ¹³C NMR (126 MHz, CDCl₃) δ 166.8 (1C, N=CH₂), 139.6 (2C, 4°), 136.4 (4C, 4°), 130.9 (2C, 3°), 130.3 (4C, 3°), 129.6 (8C, 3°), 128.7 (8C, 3°), 126.3 (2C, 3°), 89.4 (2C, 4°); ¹⁹F NMR (471 MHz, CDCl₃) δ –122.9 (br m); HRMS (m/z): [M]⁺ calcd. for C₃₃H₂₆N, 436.2060; found, 436.2058.