Unusual oxidative Smiles reaction of quinine 1,10-phenanthro-2-yl-thioether with SO₂ extrusion

References

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• Spectral data for 2: 1H NMR (600 MHz, CDCl3) δ: 9.12 (dd, J = 4.4, 1.7 Hz, 1H), 8.71 (d, J = 4.6 Hz, 1H), 8.19 (dd, J = 8.1, 1.7 Hz, 1H), 8.01 (d, J = 8.0 Hz, 1H), 7.95 (d, J= 9.2 Hz, 1H), 7.62 (d, J = 8.6 Hz, 1H), 7.54 (dd, J = 8.1, 4.4 Hz, 1H), 7.48 (d, J = 8.6 Hz, 1H), 7.41 (d, J = 4.4 Hz, 1H), 7.37 (dd, J = 9.2, 2.8 Hz, 1H), 7.30 (d, J = 2.8 Hz, 1H), 7.13 (d, J = 9.2 Hz, 1H), 7.03 (d, J = 15.5 Hz, 1H), 6.46 (dt, J = 15.5, 7.4 Hz, 1H), 6.02 (ddd, J = 17.1, 10.3, 9.5 Hz, 1H), 5.26 (dd, J = 17.1, 2.1 Hz, 1H), 5.18 (dd, J = 10.3, 2.1 Hz, 1H), 5.12–5.16 (m, 1H), 4.30–4.33 (m, 1H), 3.96 (s, 3H), 3.41 (dd, J = 13.1, 3.1 Hz, 1H), 3.21 (ddd, J = 13.1, 11.7, 3.4 Hz, 1H), 2.62–2.65 (m, 1H), 2.36–2.42 (m, 1H), 2.29–2.35 (m, 1H), 2.0–2.05 (m, 1H), 1.80–1.85 (m, 1H), 1.71–1.78 (m, 1H). 13C NMR (151 MHz, CDCl3) δ: 158.4, 157.8, 149.1, 147.7, 145.2, 144.6, 142.4, 137.7, 136.73, 136.68, 136.0, 131.3, 129.6, 127.3, 126.70, 126.7, 126.69, 122.3, 122.1, 121.9, 121.3, 117.8, 117.5, 110.4, 101.7, 55.7, 51.4, 45.0, 43.6, 39.6, 37.5, 28.0 ppm. The product undergoes gradual decomposition by standing at RT for weeks.
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