High Yield Regioselective Ring Opening of Epoxides Using Samarium Chloride Hexahydrate

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• IR values are expressed in cm−1 and 1H-NMR values are expressed in δ scale in ppm. Entry 1. 1-Azido-3-(2-naphthyloxy-2-propanol. 1H-NMR (CDCl3). δ 2.58 (m, 1H), 3.69–3.72 (m, 2H), 4.12 (m, 3H), 6.98–7.73 (m, 7H). IR (CHCl3): 3360, 2921, 2867, 2099, 1597, 1388, 1257. 1-Iodo-3-(2-naphthyloxy)-2-propanol. 1H-NMR (CDCl3): δ 2.33 (m, 1H), 3.28–3.37 (m, 2H), 3.90–4.02 (m, 3H), 7.02–7.68 (m, 7H). IR (CHCl3): 3405, 3044, 2917, 1460, 1392, 1257, 1216. Entry 2. 1-Azido-3-(3-chlorophenoxy)-2-propanol. 1H-NMR (CDCl3): δ 2.81 (m, 1H), 3.37–3.68 (m, 2H), 3.93–3.99 (m, 3H), 6.64–7.27 (m, 4H). IR (CHCl3): 3374, 3050, 2921, 2871, 2099, 1591, 1475, 1241. 1-Iodo-3-(3-chlorophenoxy)-2-propanol. 1H-NMR (CDCl3): δ 2.80 (m, 1H), 3.26–3.64 (m, 2H), 3.91 (m, 3H), 6.41–7.25 (m, 4H). IR (CHCl3): 3380, 3035, 2918, 2866, 1582, 1478, 1244. Entry 3. 1-Azido-3-(2-nitrophenoxy)-2-propanol. 1H-NMR (CDCl3): δ 3.08 (m, 1H), 3.68–3.84 (m, 2H), 4.20 (m, 3H), 6.90–7.88 (m, 4H). IR (CHCl3): 3350, 3041, 2921, 2877, 2101, 1603, 1520, 1352, 1281, 1254. 1-Iodo-3-(2-nitrophenoxy)-2-propanol. 1H-NMR (CDCl3): δ 3.17 (m, 1H), 3.23–3.42 (m, 2H), 3.99–4.22 (m, 3H), 6.88–7.87 (m, 4H). IR (CHCl3): 3504, 3050, 2938, 2872, 1602, 1518, 1349, 1281, 1253. Entry 4. 1-Azido-3-(4-chlorothiophenoxy)-2-propanol. 1H-NMR (CDCl3): δ 2.74 (m, 1H), 4.01–4.09 (m, 2H), 4.39–4.49 (m, 3H), 7.09–7.24 (d, 2H), 7.52–7.66 (d, 2H). IR (CHCl3): 3356, 2923, 2870, 2100, 1591, 1489, 1234. 1-Iodo-3-(4-chlorothiophenoxy)-2-propanol. 1H-NMR (CDCl3): δ 2.30–2.32 (m, 1H), 3.33–3.41 (m, 2H), 3.97 (m, 3H), 6.70–6.87 (d, 2H), 7.14–7.29 (d, 2H). IR (CHCl3): 3378, 2917, 2877, 1589, 1489, 1233. Entry 5. 1-Azido-3-(4-chlorophenoxy)-2-propanol. 1H-NMR (CDCl3): δ 2.84 (m, 1H), 4.01–4.09 (m, 2H), 4.39–4.49 (m, 3H), 7.09–7.24 (d, 2H), 7.52–7.66 (d, 2H). IR (CHCl3): 3356, 2923, 2870, 2100, 1591, 1489, 1242. 1-Iodo-3-(4-chlorophenoxy)-2-propanol. 1H-NMR (CDCl3): δ 2.34–2.37 (d, 1H), 3.33–3.41 (m, 2H), 3.97 (m, 3H), 6.70–6.87 (d, 2H), 7.14–7.29 (d, 2H). IR (CHCl3): 3378, 2917, 2877, 1589, 1489, 1241. Entry 6. 2-Azido-2-phenylethanol. 1H-NMR (CDCl3): δ 2.23 (s, 1H), 3.84–4.10 (m, 2H), 5.10 (m, 0.09H, minor), 5.20–5.27 (m, 0.91H, major), 7.40 (m, 5H). IR (CHCl3): 3368, 3020, 2980, 2870, 1249, 1063. 2-Iodo-2-phenylethanol. 1H-NMR (CDCl3): δ 2.22 (s, 1H), 3.85–4.04 (m, 2H), 5.05–5.10 (m, 0.08H, minor), 5.11–5.29 (m, 0.92H, major), 7.36 (m, 5H). IR (CHCl3): 3368, 3020, 2980, 2870, 2101, 1249, 1063. Entry 7. 1-Azido-2-cyclohexanol. 1H-NMR (CDCl3): δ 0.96–1.82 (m, 8H), 2.65 (s, 1H), 3.26–3.27 (m, 2H). IR (CHCl3): 3380, 2921, 2868, 2100, 1460, 1257, 1094. 1-Iodo-2-cyclohexanol. 1H-NMR (CDCl3): δ 0.95–1.79 (m, 8H), 2.62 (s, 1H), 3.23–3.25 (m, 2H). IR (CHCl3): 3376, 2962, 2851, 1458, 1016. Entry 8. 1-Azido-2-heptanol. 1H-NMR (CDCl3): δ 0.90 (m, 3H), 0.92–1.38 (m, 8H), 2.71 (s, 1H), 3.19–3.35 (m, 2.7H, major), 3.36–3.63 (m, 0.3H, minor). IR (CHCl3): 3384, 2970, 2872, 2098, 1460, 1257, 1094. 1-Iodo-2-heptanol. 1H-NMR (CDCl3): δ 0.89 (s, 3H), 0.91–1.36 (m, 8H), 2.60 (s, 1H), 3.11–3.33 (m, 2.73H, major), 3.35–3.67 (m, 0.27H, minor). IR (CHCl3): 3363, 2956, 2920, 2851, 1458, 1017. Entry 9. 1-Azido-3-chloro-2-propanol. 1H-NMR (CDCl3): δ 2.58 (s, 1H), 3.72–3.74 (m, 4H), 4.10–4.08 (m, 1H). IR (CHCl3): 3379, 2970, 2868, 2098, 1460, 1258, 1092. 3-Chloro-1-iodo-2-propanol. 1H-NMR (CDCl3): δ 2.54 (s, 1H), 3.71–3.73 (m, 4H), 4.06–4.08 (m, 1H). IR (CHCl3): 3360, 2922, 2860, 1458, 1258, 1017
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