MgBr2·OEt2-Catalyzed Thiolysis of Epoxides
909
1
-(4-chlorophenylsulfanyl)-3-isopropoxypropan-2-ol (3j)
1
H NMR: δ 1.18 (d, J = 6.5 Hz, 6H), 3.02–3.20 (m, 2H), 3.45–3.65 (m,
+
4
1
1
H), 3.86–3.92 (m, 1H), 7.26–7.45 (m, 4H). MS: m/z (%) 260 (42) [M ],
57 (97), 143 (100), 99 (63), 73 (57), 43 (76). IR (neat): ν˜ 3443, 1575,
093, 747 cm . Anal. calcd. for C12H17ClO2S: C, 55.27; H, 6.57. Found:
−
1
C, 55.2; H, 6.7.
1
-Isopropoxy-3-(naphthalen-2-ylsulfanyl)-propan-2-ol (3k)
1
H NMR: δ 1.18 (d, J = 6.5 Hz, 6H), 3.02–3.20 (m, 2H), 3.45–3.65 (m,
4
7
1
H), 3.86–3.92 (m, 1H), 7.36–7.85 (m, 7H). 13C NMR: δ 21.7, 37.3, 69.0,
1.5, 73.4, 114.0, 121.9, 125.7, 126.3, 126.5, 127.7, 129.0, 129.6, 135.7,
39.9. MS: m/z (%) 276 (13) [M ], 160 (49), 115 (53), 73 (73), 43 (100).
+
−1
IR (KBr): ν˜ 3457, 1583, 1040, 738 cm . Anal. calcd. for C16H20O2S: C,
9.53; H, 7.29. Found: C, 69.4; H, 7.4.
6
1
-Chloro-3-(4-chlorophenylsulfanyl)propan-2-ol (3m)
1
H NMR: δ 2.80–2.90 (br s, 1H), 3.10 (dd, J = 7, 14.5 Hz, 1H), 3.19
(
(
(
dd, J = 5.5, 14 Hz, 1H), 3.9–3.74 (m, 2H), 3.94–3.98 (m, 1H), 7.26–7.45
13
m, 4H). C NMR: δ 38.1, 48.2, 69.6, 129.0, 130.5, 132.2, 135.4. MS: m/z
+
%) 237 (27) [M ], 194 (31), 157 (100), 143 (45), 108 (52), 75 (37), 45 (57).
−1
IR (neat): ν˜ 3421, 1572, 1093, 742 cm . Anal. calcd. for C9H10Cl2OS:
C, 45.58; H, 4.25. Found: C, 45.7; H, 4.1.
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