10.1002/ejoc.201701007
European Journal of Organic Chemistry
FULL PAPER
1437, 1375, 1212, 1066, 1044, 1022, 863, 822, 749, 688, 477; MS (EI)
m/z (rel. int.): 155 (100%), 127 (5), 115 (10), 109 (10), 65 (5); EA:
C18H16S (264.097): calcd. C 81.77, H 6.10; found C 81.64, H 6.01.
136.6, 141.2; IR: (neat) vmax cm-1: 3081, 3055, 3026, 2896, 1581, 1571,
1489, 1479, 1454, 1445, 1438, 1086, 1071, 1024, 750, 725, 694, 686,
626; MS (EI) m/z (rel. int.): 199 (2%), 167 (100), 109 (2), 65 (2); EA:
C19H16S (276.097): calcd. C 82.57, H 5.84; found C 82.52, H 5.76.
(4-Chlorophenyl)(1-(naphthalen-2-yl)ethyl)sulfide[17]
(37)
was
obtained as white solid (0.45 g, 1.51 mmol, 98%); mp 66.2-67.7 oC (lit.
Phenyl(1-phenylpropyl)sulfide (42) was obtained as pale-yellow oil
(0.34 g, 1.48 mmol, 96%); 1H NMR: (400 MHz, C6D6): (ppm) = 0.79 (t, J
= 7.4 Hz, 3H), 1.72-2.07 (m, 2H), 3.94 (dd, J = 8.6, 6.1 Hz, 1H), 6.85-
6.95 (m, 4H), 6.96-7.01 (m, 1H), 7.06 (t, J = 7.4 Hz, 2H), 7.16 (t, J = 2.3
Hz, 1H), 7.23-7.31 (m, 2H); 13C NMR: (101 MHz, C6D6): (ppm) = 12.0,
29.5, 55.2, 126.7, 126.9, 127.9, 128.2, 128.5, 132.3, 135.6, 142.2; IR:
(neat) vmax cm-1: 3059, 3027, 2964, 2930, 2872, 1583, 1491, 1479, 1451,
1438, 1377, 1090, 1067, 1025, 738, 689, 528, 488; MS (EI) m/z (rel. int.):
119 (60%), 109 (15), 91 (100), 77 (7), 65 (15); EA: C15H16S (228.097):
calcd. C 78.90, H 7.06; found C 79.01, H 6.96.
o
67-69 C);[65] 1H NMR: (400 MHz, C6D6): (ppm) = 1.49 (d, J = 7.0 Hz,
3H), 4.14 (q, J = 7.0 Hz, 1H), 6.73-6.85 (m, 2H), 6.90-6.99 (m, 2H), 7.18-
7.28 (m, 2H), 7.35-7.46 (m, 2H), 7.48-7.64 (m, 3H); 13C NMR: (101 MHz,
C6D6): (ppm) = 21.9, 48.2, 125.4, 125.8, 125.8, 126.1, 127.6, 127.7,
128.4, 128.7, 132.9, 133.3, 133.4, 133.8, 140.3; IR: (neat) vmax cm-1:
3056, 2979, 2924, 2862, 1599, 1506, 1474, 1441, 1387, 1370, 1214,
1092, 1038, 1011, 863, 818, 746, 497, 476; MS (EI) m/z (rel. int.): 155
(100%), 143 (20), 127 (5), 115 (10), 65 (5); EA: C18H15ClS (298.058):
calcd. C 72.35, H 5.06; found C 72.44, H 5.11.
(4-Fluorophenyl)(1-(naphthalen-2-yl)ethyl)sulfide[17] (38) was obtained
as white solid (0.40 g, 1.42 mmol, 92%); mp 66.4-69.0 oC (lit. 73-75
oC);[17] 1H NMR: (400 MHz, C6D6): (ppm) = 1.51 (d, J = 7.0 Hz, 3H),
4.11 (q, J = 7.0 Hz, 1H), 6.48 (t, J = 8.7 Hz, 2H), 6.95-7.05 (m, 2H), 7.18-
7.26 (m, 2H), 7.34-7.45 (m, 2H), 7.49-7.55 (m, 1H), 7.58 (d, J = 8.4 Hz,
2H); 13C NMR: (101 MHz, C6D6): (ppm) = 21.6, 48.9, 115.6 (d, J = 21.7
Hz), 125.5, 125.7, 125.9, 126.1, 127.6, 128.3, 130.0 (d, J = 3.4 Hz),
132.9, 133.4, 135.6 (d, J = 8.1 Hz), 140.5, 162.5 (d, J = 247.3 Hz); IR:
(neat) vmax cm-1: 3058, 2972, 2924, 2867, 1585, 1487, 1445, 1374, 1218,
1154, 1087, 822, 748, 483, 477; MS (EI) m/z (rel. int.): 155 (100%), 127
(5), 115 (2), 83 (2); EA: C18H15FS (282.088): calcd. C 76.56, H 5.35;
found C 76.44, H 5.26.
Phenyl(1,2,3,4-tetrahydronaphthalen-1-yl)sulfide (43) was obtained as
pale-yellow oil (0.35 g, 1.45 mmol, 94%); 1H NMR: (400 MHz, C6D6):
(ppm) = 1.35-1.56 (m, 1H), 1.58-1.78 (m, 1H), 1.84-2.01 (m, 1H), 2.05-
2.30 (m, 1H), 2.34-2.66 (m, 2H), 4.43 (t, J = 4.2 Hz, 1H), 6.89 (dd, J = 7.1,
2.0 Hz, 1H), 6.94-7.10 (m, 5H), 7.29-7.41 (m, 2H), 7.46 (dd, J = 6.7, 2.3,
Hz, 1H); 13C NMR: (101 MHz, C6D6): (ppm) = 18.7, 28.5, 29.0, 47.5,
125.7, 126.6, 127.0, 128.8, 129.2, 130.7, 131.7, 135.5, 136.6, 137.4; IR:
(neat) vmax cm-1: 3057, 3017, 2930, 2863, 2835, 1582, 1478, 1451, 1438,
1269, 1211, 1088, 1067, 1047, 1024, 933, 772, 732, 690, 464; MS (EI)
m/z (rel. int.): 131 (100%), 115 (10), 109 (10), 91 (15), 65 (10); EA:
C16H16S (240.097): calcd. C 79.95, H 6.71; found C 79.91, H 6.66.
Phenyl(1-(p-tolyl)ethyl)sulfide[54] (44) was obtained as pale-yellow oil
(4-Methylphenyl)(1-(naphthalen-2-yl)ethyl)sulfide[17] (39) was obtained
as white solid (0.39 g, 1.42 mmol, 92%); mp 67.5-70.0 oC (lit. 69-71
oC);[17] 1H NMR: (400 MHz, C6D6): (ppm) = 1.59 (d, J = 7.0 Hz, 3H),
1.91 (s, 3H), 4.29 (q, J = 7.0 Hz, 1H), 6.71 (d, J = 7.8 Hz, 2H), 7.18-7.28
(m, 4H), 7.46-7.66 (m, 5H); 13C NMR: (101 MHz, C6D6): (ppm) = 20.6,
22.0, 48.6, 125.6, 125.8, 125.9, 127.6, 127.8, 128.2, 129.4, 131.7, 132.9,
133.3, 133.4, 137.0, 141.0; IR: (neat) vmax cm-1: 3053, 2966, 2921, 2860,
1598, 1505, 1492, 1441, 1367, 1222, 1209, 1093, 1041, 1017, 861, 821,
806, 747, 495, 479; MS (EI) m/z (rel. int.): 155 (100%), 128 (5), 115 (5),
77 (5); EA: C19H18S (278.113): calcd. C 81.97, H 6.52; found C 82.12, H
6.46.
(0.34 g, 1.51 mmol, 98%); H NMR: (400 MHz, C6D6): (ppm) = 1.49 (d,
1
J = 7.0 Hz, 3H), 2.05 (s, 3H), 4.19 (q, J = 7.0 Hz, 1H), 6.83-6.99 (m, 5H),
7.12-7.18 (m, 2H), 7.25-7.34 (m, 2H); 13C NMR: (101 MHz, C6D6):
(ppm) = 20.7, 22.4, 47.5, 126.7, 127.2, 128.6, 129.0, 132.2, 135.9, 136.4,
140.5; IR: (neat) vmax cm-1: 3055, 3020, 2968, 2922, 2865, 1583, 1512,
1479, 1438, 1371, 1208, 1185, 1115, 1089, 1062, 1043, 1024, 816, 738,
690, 540, 519, 487; MS (EI) m/z (rel. int.): 119 (100%), 109 (10), 91 (15),
65 (10); EA: C15H16S (228.097): calcd. C 78.90, H 7.06; found C 79.02, H
7.16.
(1-(4-Fluorophenyl)ethyl)(phenyl)sulfide (45) was obtained as yellow
1
oil (0.35 g, 1.52 mmol, 99%); H NMR: (400 MHz, C6D6): (ppm) = 1.37
(1-(Naphthalen-2-yl)ethyl)(octyl)sulfide (40) was obtained as colorless
(d, J = 7.0 Hz, 3H), 4.01 (q, J = 7.0 Hz, 1H), 6.69 (t, J = 8.7 Hz, 2H),
6.83-7.03 (m, 5H), 7.18-7.24 (m, 2H); 13C NMR: (101 MHz, C6D6):
(ppm) = 22.1, 47.0, 115.0 (d, J = 21.3 Hz), 127.0, 128.6, 128.8 (d, J = 8.0
Hz), 132.5, 135.2, 139.1 (d, J = 3.2 Hz), 161.9 (d, J = 245.1 Hz); IR:
(neat) vmax cm-1: 3058, 2969, 2925, 1603, 1584, 1507, 1480, 1438, 1373,
1222, 1157, 1091, 1060, 1042, 1025, 1014, 833, 737, 690, 539, 487; MS
(EI) m/z (rel. int.): 123 (100%), 109 (10), 103 (30), 77 (10); EA: C14H13FS
(232.072): calcd. C 72.38, H 5.64; found C 72.45, H 5.75.
1
oil (0.44 g, 1.48 mmol, 96%); H NMR: (400 MHz, C6D6): (ppm) = 0.86
(t, J = 7.1 Hz, 3H), 1.05-1.33 (m, 10H), 1.43 (pd, J = 7.6, 2.5 Hz, 2H),
1.56 (d, J = 7.1 Hz, 3H), 2.04-2.39 (m, 2H), 3.95 (q, J = 7.1 Hz, 1H),
7.18-7.36 (m, 2H), 7.49-7.74 (m, 5H); 13C NMR: (101 MHz, C6D6):
(ppm) = 14.0, 22.5, 22.7, 28.8, 29.2, 29.2, 29.4, 31.2, 31.8, 44.3, 125.5,
125.5, 125.8, 126.0, 128.5, 132.9, 133.4, 141.8; IR: (neat) vmax cm-1:
3055, 2955, 2923, 2853, 1740, 1600, 1508, 1452, 1374, 1269, 1239,
1126, 1048, 889, 855, 816, 746, 476; MS (EI) m/z (rel. int.): 155 (100%);
EA: C20H28S (300.191): calcd. C 79.94, H 9.39; found C 80.08, H 9.43.
(1-(4-Methoxyphenyl)ethyl)(phenyl)sulfide[54] (46) was obtained as
pale-pink oil (0.34 g, 1.40 mmol, 91%); 1H NMR: (400 MHz, C6D6):
(ppm) = 1.50 (d, J = 7.0 Hz, 3H), 3.25 (s, 3H), 4.19 (q, J = 7.0 Hz, 1H),
5.59 (d, J = 8.7 Hz, 2H), 6.86-7.01 (m, 3H), 7.12-7.15 (m, 2H), 7.25-7.34
(m, 2H); 13C NMR: (101 MHz, C6D6): (ppm) = 22.4, 47.2, 54.4, 113.8,
126.7, 128.3, 128.6, 132.3, 135.3, 136.0, 158.9; IR: (neat) vmax cm-1:
3057, 2963, 2925, 2865, 2834, 1610, 1583, 1509, 1480, 1463, 1438,
Benzhydryl(phenyl)sulfide[66] (41) was obtained as white solid (0.42 g,
1.52 mmol, 99%); mp 77.6-79.1 oC (lit. 76-77 oC);[67] 1H NMR: (400 MHz,
C6D6): (ppm) = 5.50 (s, 1H), 6.78-6.91 (m, 3H), 6.93-7.00 (m, 2H), 7.05
(t, J = 7.5 Hz, 4H), 7.20-7.26 (m, 2H), 7.32-7.42 (m, 4H); 13C NMR: (101
MHz, C6D6): (ppm) = 57.4, 126.3, 127.1, 128.4, 128.5, 128.6, 130.4,
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