10.1002/ejoc.201701643
European Journal of Organic Chemistry
FULL PAPER
683, 577, 540, 469 cm-1; HRMS (ESI): calcd for C18H14N2O3S2 Na [M +
Na]+ 393.0338, found 393.0344.
3.31 – 3.29 (m, 4H), 1.73 – 1.67 (m, 4H), 1.37 – 1.34 (m, 4H), 1.26 –
1.22 (m, 16H), 0.87– 0.84 (m, 6H);13C NMR (100 MHz, DMSO-d6) δ
143.6, 128.3, 124.1, 122.0, 50.3, 31.2, 28.4, 27.7, 22.3, 22.1, 13.9; IR v:
2924, 2854, 1728, 1581, 1476, 1466, 1188, 1055, 1026, 1007, 818 cm-1;
HRMS (ESI): calcd for C22H39NOS2 Na [M + Na]+ 421.2399, found
421.2391.
S-phenyl-S-(3- trifluoromethyl)-N-phenylthiosulfoximine (4ka) :
Yellow oil;1H NMR (400 MHz, DMSO-d6) δ 8.33 (d, J = 7.9 Hz, 1H), 8.24
(s, 1H), 8.19 – 8.02 (m, 3H), 7.88 (t, J = 7.8 Hz, 1H), 7.74 (t, J = 7.2 Hz,
1H), 7.67 (t, J = 7.2 Hz, 2H), 7.35 – 7.26 (m, 4H), 7.10 (t, J = 7.0 Hz, 1H);
13C NMR (100 MHz, DMSO-d6) δ 141.5, 140.8, 138.3, 134.3, 132.5,
131.5, 130.6( d, J = 3.3 Hz ), 130.3( d, J = 32.9Hz ), 130.1( q, J =
34.8Hz ), 130.0, 128.6( d, J = 11.1 Hz), 124.9, 124.5 ( d, J = 4.17 Hz ),
122.8, 121.8; 19F NMR (376 MHz, DMSO-d6) δ -61.43; IR v: 3063, 2962,
2326, 1580, 1476, 1446, 1323, 1129, 1096, 1006, 974 cm-1; HRMS (ESI):
calcd for C19H14F3NOS2 Na [M + Na]+ 416.0361, found 416.0370.
S, S-diphenyl-N-(4-fluorophenylthio)sulfoximine (4ab): Yellow solid,
m.p 117-120 oC; 1H NMR (400 MHz, DMSO-d6) δ 8.02 – 8.00 (m, 4H),
7.70 (t, J = 7.3 Hz, 2H), 7.63 (t, J = 7.5 Hz, 4H), 7.39 – 7.35 (m, 2H),
7.17–7.12 (m, 2H); 13C NMR (150 MHz, DMSO-d6) δ 160.1(d, J = 240.3
Hz), 139.2, 133.7, 129.8, 128.1, 125.2(d, J =7.8 Hz), 115.6, 115.5; 19F
NMR (376 MHz, DMSO-d6) δ -118.20; IR v: 3059, 2962, 2322, 1581,
1487, 1445, 1259, 1086, 1016, 963, 828 cm-1; HRMS (ESI): calcd for
C18H14FNOS2Na [M + Na]+ 366.0393, found 366.0407.
S-phenyl-S- pyridyl-N-phenylthiosulfoximine (4la): Yellow oil; 1H
NMR (400 MHz, DMSO-d6) δ 9.17 – 9.16 (m, 1H), 8.87 – 8.86 (m, 1H),
8.40– 8.39 (m, 1H), 8.14 – 8.08 (m, 2H), 7.74 – 7.67 (m, 4H), 7.36 – 7.27
(m, 4H), 7.14 – 7.07 (m, 1H); 13C NMR (100 MHz, DMSO-d6) δ 154.1,
148.6, 141.5, 138.5, 136.2 (d, J=32.2Hz), 134.2, 130.0, 128.6, 128.4,
124.8 (d, J=22.1 Hz), 122.7; IR v: 3055, 3001, 2965, 1577, 1565, 1475,
1443, 1211, 1088, 971, 735, 679, 578, 541, 470 cm-1; HRMS (ESI): calcd
for C17H14N2OS2 Na [M + Na]+ 349.0440, found 349.0446.
S, S-diphenyl-N-(4- chlorophenylthio)sulfoximine (4ac). Yellow solid,
m.p 125-127 oC (Lit.14 121-123 oC); 1H NMR (400 MHz, DMSO-d6) δ
8.02 (d, J = 7.9 Hz, 4H), 7.71 (t, J = 7.2 Hz, 2H), 7.64 (t, J = 7.5 Hz, 4H),
7.35 – 7.34 (m, 4H); 13C NMR (100 MHz, DMSO-d6) δ 141.4, 139.1,
133.9, 129.9, 128.9, 128.4, 128.1, 124.2; IR v: 3062, 1469, 1445, 1386,
1221, 1082, 954, 811, 729, 682, 575, 531, 482 cm-1; HRMS (ESI): calcd
for C18H14ClNOS2 Na [M + Na]+ 382.0098, found 382.0106.
S-methyl-S-phenyl-N-phenylthiosulfoximine (4ma): Yellow oil; 1H
NMR (400 MHz, DMSO-d6) δ 7.98 – 7.88 (m, 2H), 7.78 – 7.70 (m, 1H),
7.69 – 7.61 (m, 2H), 7.30 – 7.24 (m, 4H), 7.00 – 7.03 (m, 1H), 3.49 (s,
3H); 13C NMR (100 MHz, DMSO-d6) δ 142.7, 138.7, 133.7, 129.5, 128.4,
128.1, 124.4, 122.3, 42.8; IR v: 3020, 2997, 2916, 1468, 1444, 1220,
1082, 974, 953, 806, 787, 684, 525, 505, 486 cm-1; HRMS (ESI): calcd
for C13H13NOS2 Na [M + Na]+ 286.0331, found 286.0332.
S, S-diphenyl-N-(4-bromophenylthio)sulfoximine (4ad):Yellow solid,
m.p 119-121 oC (Lit.14 122-123 oC); 1H NMR (600 MHz, DMSO-d6) δ 8.02
(d, J = 7.7 Hz, 4H), 7.71 (t, J = 7.2 Hz, 2H), 7.64 (t, J = 7.4 Hz, 4H), 7.46
(d, J = 8.3 Hz, 2H), 7.29 (d, J = 8.2 Hz, 2H); 13C NMR (100 MHz, DMSO-
d6) δ 142.0, 139.1, 133.9, 131.3, 129.9, 128.2, 124.5, 117.1; IR v: 3084,
3062, 1466, 1445, 1218, 1087, 1076, 955, 808, 732, 681, 576, 539, 473
cm-1; HRMS (ESI): calcd for C18H14BrNOS2 Na [M + Na]+ 425.9592,
found 425.9595.
S-cyclohexyl-S-phenyl-N-phenylthiosulfoximine (4na): White solid,
1
m.p 104-108 oC; H NMR (400 MHz, DMSO-d6) δ 7.73– 7.67(m, 3), 7.60
(t, J = 7.5 Hz, 2H), 7.19 (d, J = 4.2 Hz, 4H), 6.98 (m, 1H), 3.3 (t, J = 10.4
Hz, 1H), 2.23 (d, J = 11.9 Hz, 1H), 1.78– 1.66 (m, 3H), 1.53 (d, J = 12.7
Hz, 1H), 1.42 – 1.12 (m, 4H), 1.06 – 1.00 (m, 1H); 13C NMR (150 MHz,
DMSO-d6) δ 143.2, 135.3, 133.8, 129.5, 129.4, 128.3, 124.2, 122.1, 62.4,
26.0, 25.1, 24.7, 24.4, 24.3; IR v:3060, 2926, 2851, 1728, 1578,1475,
1438, 1259, 1219, 1191, 1082, 1021, 960, 894, 853 cm-1; HRMS (ESI):
calcd for C18H21NOS2 Na [M + Na]+ 354.0957, found 354.0968.
S, S-diphenyl-N-(2-bromophenylthio)sulfoximine (4ae): Yellow solid,
m.p 120-123 oC; 1H NMR (400 MHz, DMSO-d6) δ 8.06 (d, J = 7.5 Hz, 4H),
7.75 – 7.62 (m, 7H), 7.48 – 7.46 (d, J = 7.8 Hz, 1H), 7.41 (t, J = 7.4 Hz,
1H), 7.04 (t, J = 7.1 Hz, 1H); 13C NMR (150 MHz, DMSO-d6) δ 142.6,
139.2, 133.9, 131.7, 129.9, 128.1, 127.8, 125.8, 124.1, 114.9; IR v: 3052,
2921, 2852, 1439, 1424, 1219, 1088, 956, 743, 724, 681, 575, 540, 490
cm-1; HRMS (ESI): calcd for C18H14BrNOS2 Na [M + Na]+ 425.9592,
found 425.9597.
S-n-octyl-S-phenyl-N-phenylthiosulfoximine(4oa) : Yellow oil; 1H
NMR (600 MHz, DMSO-d6) δ 7.87 (d, J = 7.5 Hz, 2H), 7.74 (t, J = 7.2 Hz,
1H), 7.66 (t, J = 7.6 Hz, 2H), 7.28– 7.24 (m, 4H), 7.05 (t, J = 6.7 Hz, 1H),
3.67– 3.56 (m, 2H), 1.67 – 1.66 (m, 1H), 1.52 – 1.51 (m, 1H), 1.32 – 1.17
(m, 10 H), 0.84 – 0.81 (m, 3 H); 13C NMR (150 MHz, DMSO-d6) δ 143.2,
135.3, 133.8, 129.5, 129.4, 128.3, 124.2, 122.1, 62.4, 26.0, 25.1, 24.7,
24.4, 24.3; IR v: 3058, 2924, 2854, 1581, 1476, 1445, 1208, 1090, 974
cm-1; HRMS (ESI): calcd for C20H27NOS2 Na [M + Na]+ 384.1426, found
384.1429.
S, S-diphenyl-N-(4-cyanphenylthio)sulfoximine (4af): White solid,
m.p 134-137 oC; 1H NMR (400 MHz, DMSO-d6) δ 8.05 (d, J = 7.5 Hz, 4H),
7.75 – 7.64 (m, 8H), 7.50 (d, J = 8.4 Hz, 2H); 13C NMR (100 MHz,
DMSO-d6) δ 150.3 , 138.9, 134.1, 132.1, 130.0, 128.2, 122.3, 119.2,
106.3; IR v: 3075, 3055, 2226, 1590, 1445, 1215, 1080, 971, 729, 683,
576, 536, 458 cm-1; HRMS (ESI): calcd for C19H14N2OS2Na [M + Na]+
373.0440, found 373.0445.
S, S-diphenyl-N- naphthylthiosulfoximine (4ag) : Yellow solid,
m.p146-149 oC; 1H NMR (400 MHz, DMSO-d6) δ 8.06 (d, J = 7.8 Hz, 4H),
7.82 (t, J = 8.4 Hz, 4H), 7.71 (t, J = 7.2 Hz, 2H), 7.66 –7.63 (m, 4H), 7.50
– 7.37 (m, 3H); 13C NMR (100 MHz, DMSO-d6) δ 140.0, 139.3, 133.8,
133.3, 131.0, 129.9, 128.3, 128.0, 127.7, 126.8, 126.7, 125.1, 121.7,
119.7; IR v: 3065, 3046, 1618, 1587, 1446, 1211, 1084, 967, 809, 729,
680, 587, 577, 470 cm-1; HRMS (ESI): calcd for C19H14N2OS2Na [M +
Na]+ 398.0644, found 398.0653.
N-phenylthiotetrahydrothiophene sulfoximine (4pa) : Yellow solid,
m.p 82-85 oC; 1H NMR (600 MHz, DMSO-d6) δ 7.29 – 7.28 (m, 4H), 7.08
– 7.07 (m, 1H), 3.42 – 3.38 (m, 2H), 3.23 – 3.19(m, 2H), 2.20 – 2.19 (m,
2H), 2.11 – 2.10 (m, 2H); 13C NMR (100 MHz, DMSO-d6) δ 142.9, 128.6,
124.4, 121.9, 51.5, 23.5; IR v: 2998, 2961, 2937, 1580, 1475, 1438, 1260,
1193, 1085, 953, 903 cm-1; HRMS (ESI): calcd for C10H13NOS2 Na [M +
Na]+ 250.0331, found 250.0327.
1
S, S- dimethyl-N-phenylthiosulfoximine (4qa): Yellow oil; H NMR
S, S-diphenyl-N-(2- tertiary butylphenylthio)sulfoximine (4ah) :
Yellow solid, m.p 134-136 oC; 1H NMR (400 MHz, DMSO-d6) δ 8.01 (d, J
= 7.2 Hz, 4H), 7.70 (t, J = 7.3 Hz, 2H), 7.63 (t, J = 7.4 Hz, 4H), 7.31 (d, J
= 8.6 Hz, 2H), 7.26 (d, J = 8.6 Hz, 2H),1.25 (s, 9H); 13C NMR (150 MHz,
DMSO-d6) δ 147.5, 139.4, 138.5, 133.6, 129.7, 128.1, 125.4, 123.1, 34.0,
31.1; IR v: 2953, 2897, 2865, 1495, 1446, 1214, 1086, 956, 821, 729,
684, 640, 575 cm-1; HRMS (ESI): calcd for C22H23NOS2Na [M+Na]+
404.1113, found 404.1133.
(600 MHz, DMSO-d6) δ 7.27 – 7.26 (m, 4H), 7.09 – 7.02 (m, 1H), 3.23 (s,
6H); 13C NMR (150 MHz, DMSO-d6) δ 143.6, 128.5, 124.2, 121.9, 40.2;
IR v: 3010, 2922, 1579, 1475, 1437, 1199, 1018, 961, 736, 689, 489 cm-1;
HRMS (ESI): calcd for C8H11NOS2 Na [M + Na]+ 224.0174, found
224.0175.
S, S-di-n-octyl-N-phenylthiosulfoximine (4ra): Yellow oil; 1H NMR
(400 MHz, DMSO-d6) δ 7.26 (d, J = 4.2 Hz, 4H), 7.07 – 7.02 (m, 1H),
This article is protected by copyright. All rights reserved.