9-Isopropylidene-5-nitro-1,4-dihydro-1,4-methano-naphthalene → 9-Isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-amine

참여 물질

반응 단계

9-Isopropylidene-5-nitro-1,4-dihydro-1,4-methano-naphthalene (5) (6.5 g, 29 mmol) was stirred in tetrahydrofuran (150 mL) at room temperature with rhodium (5%) on carbon (3 g). The head space was evacuated and was replaced with hydrogen. Positive pressure was maintained by the use of a balloon filled with hydrogen. After 4 days, the reaction mixture was filtered and was evaporated to afford the title compound as an 87:13 syn:anti mixture (5.6 g, 97.4%) as a pale brown oil: 1H NMR (600 MHz, CDCl3) δ 6.91-6.87 (m, 1H), 6.63 (d, J=7.2 Hz, 1H), 6.47 (d, J=8.0 Hz, 1H), 3.51 (s, 2H), 3.18 (s, 1H), 3.13 (s, 1H), 1.94-1.87 (m, 2H), 1.52 (d, J=9.9 Hz, 1H), 1.21-1.13 (m, 2H), 1.05-0.97 (m, 1H), 0.80 (d, J=2.0 Hz, 3H), 0.79 (d, J=2.0 Hz, 3H); 13C NMR (151 MHz, CDCl3) δ 147.94, 140.30, 130.32, 126.60, 113.52, 112.86, 69.17, 46.79, 42.23, 27.94, 27.02, 25.65, 22.54, 22.26; EIMS m/z 201; two peaks; 83:17 ratio.

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