10.1002/adsc.201800437
Advanced Synthesis & Catalysis
bis(4-Methoxyphenyl)methane (7r)[32]
:
(m, 4H), 2.89 (t, J = 6.6 Hz, 2H), 2.69 (t, J = 6.6 Hz, 2H).
13C NMR (75 MHz, CDCl3) δ = 159.4 (Cq), 146.6 (Cq),
134.4 (Cq), 125.2 (CH), 115.3 (CH), 109.0 (CH), 73.4 (Cq),
55.6 (CH3), 48.5 (CH2), 40.90 (2 CH2), 30.1 (CH2). IR (neat):
2959, 2919, 2831, 1610, 1583, 1488, 1464, 1421, 1324,
1294, 1271, 1242, 1203, 1177, 1141, 1096, 1082, 1030, 961,
936, 888, 824, 803, 767, 741, 699 cm-1. HRMS (APCI): m/z
[M+H]+ calcd for C12H15OS2: 239.0559; found: 239.0553.
Colorless oil, yield 67%, 76.5 mg.
1H NMR (300 MHz, CDCl3) δ = 7.11 (d, J = 8.4 Hz, 4H),
6.84 (d, J = 8.4 Hz, 4H), 3.88 (s, 2H), 3.79 (s, 6H). 13C NMR
(75 MHz, CDCl3) δ = 158.0 (2 Cq), 133.8 (2 Cq), 129.8 (4
CH), 114.0 (4 CH), 55.4 (2 CH3), 40.2 (CH2). IR (neat):
2954, 2906, 2834, 1611, 1583, 1463, 1439, 1300, 1275,
1243, 1175, 1108, 1035, 852, 808, 762, 747, 701 cm-1.
Spiro[thiochromane-4,2'-[1,3]dithiolane] (8e):
9H-Fluorene (7s)[33]
:
White solid, mp 45.4 – 45.5 °C, yield 99%, 238.0 mg.
1H NMR (300 MHz, CDCl3) δ = 8.09 – 7.98 (m, 1H), 7.07
– 6.99 (m, 3H), 3.62 – 3.42 (m, 4H), 3.24 – 3.16 (m, 2H),
2.74 – 2.65 (m, 2H). 13C NMR (75 MHz, CDCl3) δ = 135.7
(Cq), 133.3 (Cq), 131.5 (CH), 127.7 (CH), 126.5 (CH),
124.3 (CH), 67.7 (Cq), 42.0 (CH2), 40.9 (2 CH2), 25.8 (CH2).
IR (neat): 3053, 2917, 1588, 1560, 1463, 1422, 1296, 1277,
1264, 1226, 1158, 1123, 1061, 1038, 1006, 968, 901, 850,
811, 780, 739, 711 cm-1. HRMS (APCI): m/z [M+H]+ calcd
for C11H13S3: 241.0173; found: 241.0168.
Colorless oil, for yield: see the text.
1H NMR (300 MHz, CDCl3) δ = 7.81 (d, J = 7.5 Hz, 2H),
7.57 (d, J = 7.5 Hz, 2H), 7.43 – 7.29 (m, 4H), 3.92 (s, 2H).
13C NMR (75 MHz, CDCl3) δ = 143.3 (2 Cq), 141.8 (2 Cq),
126.8 (4 CH), 125.1 (2 CH), 120.0 (2 CH), 37.1 (CH2). IR
(neat): 1478, 1448, 1402, 1189, 954, 907, 733, 696 cm-1.
1-Benzyl-3,5-dimethoxybenzene (7t)[25]
Colorless oil, yield 71%, 81.0 mg.
:
1H NMR (300 MHz, CDCl3) δ = 7.24 – 7.09 (m, 5H), 6.28
– 6.23 (m, 3H), 3.84 (s, 2H), 3.68 (s, 6H). 13C NMR (75
MHz, CDCl3) δ = 161.0 (2 Cq), 143.5 (Cq), 140.8 (Cq),
129.0 (2 CH), 128.6 (2 CH), 126.2 (CH), 107.3 (2 CH), 98.1
(CH), 55.4 (2 CH3), 42.31 (CH2). IR (neat): 2999, 2959,
2924, 2836, 1609, 1594, 1494, 1467, 1453, 1428, 1348,
1321, 1290, 1252, 1205, 1157, 1097, 1065, 1058, 1031, 993,
948, 923, 863, 851, 820, 797, 757, 735, 705 cm-1.
2-Methyl-2-(naphthalen-2-yl)-1,3-dithiane (8f):
White solid, mp 90.7 – 90.9 °C, yield 99%, 257.8 mg.
1H NMR (300 MHz, CDCl3) δ = 8.41 (s, 1H), 8.06 (dd, J =
8.7Hz, J = 1.8 Hz, 1H), 7.91 – 7.83 (m, 3H), 7.52 – 7.48 (m,
2H), 2.79 – 2.75 (m, 4H), 2.01 – 1.93 (m, 2H), 1.88 (s, 3H).
13C NMR (75 MHz, CDCl3) δ = 141.2 (Cq), 133.4 (Cq),
132.5 (Cq), 128.5 (CH), 128.4 (CH), 127.5 (CH), 127.1
(CH), 126.3 (CH), 126.2 (CH), 125.8 (CH), 54.2 (Cq), 32.8
(CH3), 28.2 (2 CH2), 24.8 (CH2). IR (neat): 3053, 2974,
2912, 2895, 1596, 1501, 1440, 1418, 1366, 1343, 1265,
1244, 1162, 1126, 1063, 1045, 1017, 997, 969, 949, 904,
861, 819, 750, 730, 702 cm-1. HRMS (APCI): m/z [M+H]+
calcd for C15H17S2: 261.0766; found: 261.0769.
3,4-Dihydro-2H-spiro[naphthalene-1,2'-
[1,3]dithiane] (8a)[24]
:
Yellow oil, yield 99%, 234.0 mg.
1H NMR (300 MHz, CDCl3) δ = 7.90 (d, J = 9 Hz, 1H), 7.14
– 6.94 (m, 3H), 3.11 (td, J = 13.8 Hz, J = 2.4 Hz, 2H), 2.77
– 2.52 (m, 6H), 2.14 – 2.05 (m, 1H), 1.96 – 1.83 (m, 3H).
13C NMR (75 MHz, CDCl3) δ = 137.9 (Cq), 137.7 (Cq),
130.0 (CH), 129.1 (CH), 127.9 (CH), 126.3 (CH), 52.4 (Cq),
36.3 (CH2), 30.1 (CH2), 28.1 (2 CH2), 25.2 (CH2), 20.3
(CH2). IR (neat): 2929, 2834, 1484, 1448, 1419, 1273, 1237,
1156, 1066, 1019, 942, 902, 868, 809, 761, 740, 697, 675
cm-1. HRMS (APCI): m/z [M+H]+ calcd for C13H17S2:
237.0766; found: 237.0772.
1,2,3,4-Tetrahydronaphthalene (9a)[34]
:
Colorless oil, for yield: see the text.
1H NMR (300 MHz, CDCl3) δ = 7.68 – 6.88 (m, 4H), 3.10 -
2.90 (m, 4H), 2.12 – 1.95 (m, 4H). 13C NMR (75 MHz,
CDCl3) δ = 137.1 (2 Cq), 129.2 (2 CH), 125.5 (2 CH), 29.5
(2 CH2), 23.35 (2 CH2). IR (neat): 3016, 2927, 2858, 2838,
1494, 1452, 1435, 1283, 1111, 1037, 945, 865, 804, 739 cm-
1
.
3,4-Dihydro-2H-spiro[naphthalene-1,2'-[1,3]dithiolane]
(8b):
5-Methoxy-1,2,3,4-tetrahydronaphthalene (9b)[35]
:
White solid, mp 58.3 – 58.5 °C, yield 99%, 220.1 mg.
1H NMR (300 MHz, CDCl3) δ = 7.96 (d, J = 8.1 Hz, 1H),
7.24 – 7.08 (m, 2H), 7.00 (d, J = 7.5 Hz, 1H), 3.66 – 3.42
(m, 4H), 2.81 (t, J = 6.3 Hz, 2H), 2.48 – 2.35 (m, 2H), 2.06
– 1.98 (m, 2H). 13C NMR (75 MHz, CDCl3) δ = 139.1 (Cq),
137.4 (Cq), 130.9 (CH), 128.7 (CH), 127.3 (CH), 126.2
(CH), 68.8 (Cq), 43.9 (CH2), 41.0 (2 CH2), 29.6 (CH2), 22.9
(CH2). IR (neat): 3060, 3017, 2919, 2861, 2835, 1482, 1451,
1438, 1418, 1275, 1240, 1155, 1066, 1016, 954, 901, 849,
820, 788, 740 cm-1. HRMS (APCI): m/z [M+H]+ calcd for
C12H15S2: 223.0610; found: 223.0617.
Colorless oil, yield 76%, 61.6 mg.
1H NMR (300 MHz, CDCl3) δ = 7.07 (t, J = 7.8 Hz, 1H),
6.72 – 7.63 (m, 2H), 3.81 (s, 3H), 2.78 – 2.62 (m, 4H), 1.89
– 1.66 (m, 4H). 13C NMR (75 MHz, CDCl3) δ = 157.5 (Cq),
138.6 (Cq), 126.1 (Cq), 125.8 (CH), 121.5 (CH), 106.9 (CH),
55.4 (CH3), 29.8 (CH2), 23.2 (CH2), 23.0 (2 CH2). IR (neat):
2930, 2857, 2836, 2181, 2058, 2020, 1604, 1586, 1468,
1437, 1336, 1309, 1272, 1252, 1170, 1096, 1058, 1000, 959,
880, 856, 826, 764, 710 cm-1.
5-Methoxy-2,3-dihydro-1H-indene (9c)[36]
Colorless oil, yield 85%, 63.0 mg.
:
1H NMR (300 MHz, CDCl3) δ = 7.11 (d, J = 8.1 Hz, 1H),
6.80 (s, 1H), 6.70 (d, J = 8.1 Hz, 1H), 3.78 (s, 3H), 2.91 –
2.81 (m, 4H), 2.14 – 1.96 (m, 2H). 13C NMR (75 MHz,
CDCl3) δ = 158.7 (Cq), 145.8 (Cq), 136.3 (Cq), 124.8 (CH),
112.0 (CH), 110.0 (CH), 55.6 (CH3), 33.3 (CH2), 32.1 (CH2),
26.0 (CH2). IR (neat): 2955, 2935, 2906, 2845, 1608, 1585,
1492, 1465, 1443, 1411, 1329, 1294, 1277, 1255, 1243,
1213, 1194, 1164, 1143, 1097, 1082, 1034, 921, 861, 914,
802, 755, 731 cm-1.
5-Methoxy-3,4-dihydro-2H-spiro[naphthalene-1,2'-
[1,3]dithiolane] (8c):
White solid, mp 108.6 – 108.8 °C, yield 99%, 249.9 mg.
1H NMR (300 MHz, CDCl3) δ = 7.60 (d, J = 8.1 Hz, 1H),
7.17 (t, J = 8.1 Hz, 1H), 6.68 (d, J = 8.1 Hz, 1H), 3.81 (s,
3H), 3.63 – 3.41 (m, 4H), 2.70 (t, J = 6.3 Hz, 2H), 2.45 –
2.30 (m, 2H), 2.12 – 1.95 (m, 2H). 13C NMR (75 MHz,
CDCl3) δ = 156.4 (Cq), 140.4 (Cq), 126.9 (Cq), 126.0 (CH),
122.6 (CH), 108.0 (CH), 68.8 (Cq), 55.4 (CH3), 43.3 (CH2),
40.9 (2 CH2), 23.0 (CH2), 22.2 (CH2). IR (neat): 2997, 2936,
2918, 2834, 1681, 1600, 1580, 1464, 1434, 1346, 1311,
1254, 1237, 1175, 1106, 1060, 1025, 974, 906, 878, 852,
804, 786, 760, 730, 701 cm-1. HRMS (APCI): m/z [M+H]+
calcd for C13H17OS2: 253.0715; found: 253.0715.
Thiochromane (9d)[37]
:
Colorless oil, yield 85%, 63.9 mg.
1H NMR (300 MHz, CDCl3) δ = 7.20 – 6.88 (m, 4H), 3.03
(t, J = 6.0 Hz, 2H), 2.82 (t, J = 6.0 Hz, 2H), 2.17 – 2.08 (m,
2H). 13C NMR (75 MHz, CDCl3) δ = 134.0 (Cq), 133.0 (Cq),
130.1 (CH), 126.7 (CH), 126.5 (CH), 124.0 (CH), 29.8
(CH2), 27.7 (CH2), 23.0 (CH2). IR (neat): 3060, 3006, 2934,
2853, 1587, 1566, 1479, 1438, 1393, 1296, 1268, 1123,
1074, 1049, 932, 836, 781, 744 cm-1.
6-Methoxy-2,3-dihydrospiro[indene-1,2'-
[1,3]dithiolane] (8d):
White solid, mp 78.6 – 78.9 °C, yield 99%, 236.0 mg.
1H NMR (300 MHz, CDCl3) δ = 7.22 – 6.89 (m, 2H), 6.78
(dd, J = 8.4 Hz, J = 2.4 Hz, 1H), 3.82 (s, 3H), 3.60 – 3.37
9
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