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Organic & Biomolecular Chemistry
Page 3 of 4
DOI: 10.1039/C7OB02834B
Journal Name
ARTICLE
Isopropyl(p-tolyl)sulfane (3b):11 After purification by silica gel 2H), 3.68 (s, 2H). 3.36 (q, J = 7.2 Hz, 2H), 3.31 (q, J = 7.2 Hz, 2H), 2.32
(s, 3H), 1.18 (t, J = 7.2 Hz 3H), 1.10 (t, J = 7.2 Hz, 3H); 13C NMR (100
column chromatography (N-Pentane), compound 3b was isolated as
a colorless oil (78 mg, 95%); Rf (PE) = 0.36. 1H NMR (400 MHz,
MHz, CDCl3): δ 167.7, 137.3, 131.5, 131.4, 129.8, 42.6, 40.4, 37.8,
CDCl3): δ 7.32-7.29 (m, 2H), 7.11-7.09 (m, 2H), 3.34-3.24 (m, 1H),
21.1, 14.5, 13.0.
2.32 (s, 3H), 1.26 (d, J = 6.8 Hz, 6H); 13C NMR (100 MHz, CDCl3): δ
137.1, 132.9, 131.8, 129.7, 38.8, 23.3, 21.2.
1-methyl-3-((trifluoromethyl)thio)-1H-indole
(3k):8
After
Cyclopropyl(phenyl)sulfane (3c):12 After purification by silica gel
column chromatography (PE), compound 3c was isolated as a
colorless oil (66 mg, 88%); Rf (PE) = 0.45. 1H NMR (400 MHz, CDCl3):
δ 7.37-7.34 (m, 2H), 7.26 (t, J = 7.2 Hz, 2H), 7.13-7.09 (m, 1H), 2.20-
2.14 (m, 1H), 1.06-1.01 (m, 2H), 0.70-0.65 (m, 2H); 13C NMR (100
MHz, CDCl3): δ 138.9, 128.8, 126.8, 125.1, 12.3, 8.6.
purification by silica gel column chromatography (PE : EA = 20 : 1),
compound 3k was isolated as a yellow solid (86.5mg, 75%); Rf (PE :
1
EA = 10 : 1) = 0.50; H NMR (400 MHz, CDCl3): δ 7.79 (d, J = 7.6 Hz,
1H), 7.38-7.25 (m, 4H), 3.83 (s, 3H); 13C NMR (100 MHz, CDCl3): δ
137.4, 137.1, 130.4, 129.6 (q, J = 308.0 Hz, 1C), 123.1, 121.4, 119.6,
110.0, 93.3 (q, J = 2.0 Hz, 1C), 33.4; 19F NMR (376 MHz, CDCl3): δ -
44.96 (s, 3F).
Allyl(p-tolyl)sulfane (3d):13 After purification by silica gel column
chromatography (PE), compound 3d was isolated as a yellow solid
(72.8 mg, 89%); Rf (PE) = 0.44. 1H NMR (400 MHz, CDCl3): δ 7.27-
7.26 (m, 1 H), 7.26-7.24 (m, 1H), 7.10 (d, J = 8.0 Hz, 2H), 5.92-5.81
(m, 1H), 5.11-5.06 (m, 1H), 5.06-5.02 (m, 1H), 3.52-3.49 (m, 2H),
2.31 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 136.6, 134.0, 132.3,
130.9, 129.7, 117.5, 38.1, 21.2.
3-((difluoromethyl)thio)-1H-indole (3l):7f After purification by silica
gel column chromatography (PE : EA = 8 : 1), compound 3l was
isolated as a brown solid (90 mg, 91%); Rf (PE : EA = 8 : 1) = 0.34; 1H
NMR (400 MHz, CDCl3): δ 8.45 (s, 1H), 7.80-7.78 (m, 1H), 7.46 (d, J =
2.8 Hz, 1H), 7.42-7.40 (m, 1H), 7.30-7.23 (m, 2H), 6.68 (t, J = 57.6 Hz,
1H); 13C NMR (100 MHz, CDCl3): δ 136.2, 132.0,129.8, 123.4, 121.4,
121.2 (t, J =274.0 Hz, 1C), 119.4, 111.8, 96.7 (t, J = 3.7 Hz, 1C); 19F
NMR (376 MHz, CDCl3): δ = -91.96 (d, J = 60.1 Hz, 2F).
Prop-2-yn-1-yl(p-tolyl)sulfane (3e):14 After purification by silica gel
column chromatography (PE), compound 3e was isolated as a
Diphenylsulfane (3m):4d After purification by silica gel column
chromatography (PE), compound 3m was isolated as a colorless oil
1
yellow oil (59 mg, 73%); Rf (PE) = 0.45. H NMR (400 MHz, CDCl3): δ
7.39-7.36 (m, 2H), 7.14 (d, J = 8.0 Hz, 2H), 3.55 (d, J = 2.8 Hz, 2H),
2.34 (s, 3H), 2.22 (t, J =1.2 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ
137.5, 131.4, 131.3, 129.9, 80.2, 71.6, 23.5, 21.2.
1
(92mg, 99 %); Rf (PE) = 0.40; H NMR (400 MHz, CDCl3): δ 7.34-7.31
(m, 5H), 7.29-7.25 (m, 3H), 7.23-7.19 (m, 2H); 13C NMR (100 MHz,
CDCl3): δ 136.0, 131.2, 129.3, 127.1.
Benzyl(p-tolyl)sulfane (3f):5 After purification by silica gel column
chromatography (PE : EA = 100 : 1), compound 3f was isolated as a
white solid (105 mg, 99%); Rf (PE) = 0.28. 1H NMR (400 MHz, CDCl3):
δ 7.25-7.18 (m, 7H), 7.04 (d, J = 8.0 Hz, 2H), 4.04 (s, 2H), 2.28 (s,
3H); 13C NMR (100 MHz, CDCl3): δ 138.0, 136.7, 132.7, 130.9, 129.7,
129.0, 128.6, 127.2, 40.0, 21.2.
Bis(4-nitrophenyl)sulfane (3n):4d After purification by silica gel
column chromatography (PE : DCM = 2 : 1), compound 3n was
isolated as a yellow solid (128 mg, 93 %); Rf (PE : DCM = 3 : 1) =
1
0.33; H NMR (400 MHz, d6-DMSO): δ 8.25 (dd, J = 8.4, 1.6 Hz, 4H),
7.64 (dd, J = 8.4, 2.0 Hz, 4H); 13C NMR (100 MHz, d6-DMSO): δ 146.7,
142.2, 131.3, 124.8.
1-benzyl-2-(benzylthio)-1H-benzo[d]imidazole
(3g):15
After
Bis(4-methoxyphenyl)sulfane (3o):4d After purification by silica gel
column chromatography (PE : EA = 10 : 1), compound 3o was
isolated as a white solid (121 mg, 99 %); Rf (PE : EA = 10 : 1) = 0.41;
1H NMR (400 MHz, CDCl3): δ 7.29-7.25 (m, 4H), 6.85-6.81 (m, 4H),
3.78 (s, 6H); 13C NMR (100 MHz, CDCl3): δ 159.2, 132.9, 127.6,
114.9, 55.5.
purification by silica gel column chromatography (PE : EA = 10 : 1),
compound 3g was isolated as a white solid (156 mg, 95%); Rf (PE :
EA = 10 : 1 ) = 0.41; 1H NMR (400 MHz, CDCl3): δ 7.74 (d, J = 8.0 Hz,
1H), 7.41-7.37 (m, 2H), 7.31-7.26 (m, 3H), 7.26-7.20 (m, 4H), 7.17-
7.15 (m, 2H), 7.10-7.08 (m, 2H), 5.23 (s, 2H), 4.62 (s, 2H); 13C NMR
(100 MHz, CDCl3): δ 151.8, 143.8, 136.9, 136.3, 135.8, 129.2, 128.9,
128.8, 128.0, 127.8, 127.0, 122.3, 122.2, 118.6, 109.4, 47.7, 37.7.
Bis(2,6-dimethylphenyl)sulfane (3p):19 After purification by silica gel
column chromatography (PE), compound 3p was isolated as a white
solid (119 mg, 99 %); Rf (PE) = 0.61; 1H NMR (400 MHz, CDCl3): δ
7.06-6.99 (m, 6H), 2.22 (s, 12H); 13C NMR (100 MHz, CDCl3): δ 140.5,
134.5, 128.6, 127.0, 21.8.
Ethyl 2-(p-tolylthio)acetate (3h):16 After purification by silica gel
column chromatography (PE : EA = 10 : 1), compound 3h was
isolated as a white oil (85mg, 81%); Rf (PE : EA = 10 : 1) = 0.44; 1H
NMR (400 MHz, CDCl3): δ 7.34-7.31 (m, 2H), 7.10 (d, J = 8.0 Hz, 2H),
4.15 (q, J =7.2 Hz, 2H), 3.57 (s, 2H), 2.31 (s, 3H), 1.22 (t, J = 7.2 Hz,
3H); 13C NMR (100 MHz, CDCl3): δ 169.9, 137.4, 131.4, 131.1, 129.9,
61.5, 37.6, 21.1, 14.2.
4,4'-thiodiphenol (3q)20 after purification by silica gel column
chromatography (PE : EA = 1 : 1), compound 3q was isolated as a
1
white solid (102 mg, 94%); Rf (PE : EA = 1 : 1) = 0.52; H NMR (400
2-(p-tolylthio)acetic acid (3i):17 after purification by silica gel
column chromatography (EA), compound 3i was isolated as a yellow
solid (74 mg, 81%); Rf (EA) = 0.26; 1H NMR (400 MHz, CDCl3): δ
11.17 (s, 1H), 7.33 (d, J = 8.0 Hz, 2H), 7.11 (d, J = 8.0 Hz, 2H), 3.60 (s,
2H), 2.32 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 175.6, 137.6, 131.1,
131.0, 130.1, 37.5, 21.2.
MHz, d6-DMSO): δ 9.62 (s, 2H), 7.14 (d, J = 8.4 Hz, 4H), 6.73 (d, J =
8.4 Hz, 4H); 13C NMR (100 MHz, d6-DMSO): δ 157.0, 132.7, 124.7,
116.3.
9H-thioxanthen-9-one (3r):4d After purification by silica gel column
chromatography (PE : EA = 10 : 1), compound 3r was isolated as a
yellow solid (104 mg, 99 %); Rf (PE : EA = 10 : 1) = 0.37; 1H NMR (400
MHz, CDCl3): δ 8.64-8.61 (m, 2H), 7.65-7.57 (m, 4H), 7.51-7.47 (m,
2H); 13C NMR (100 MHz, CDCl3): δ 180.1, 137.4, 132.4, 130.0, 129.5,
126.4, 126.1.
N,N-diethyl-2-(p-tolylthio)acetamide (3j):18 after purification by
silica gel column chromatography (PE : EA = 3 : 1), compound 3j was
isolated as a colorless oil (78 mg, 66 %); Rf (PE : EA = 5 : 1) = 0.24; 1H
NMR (400 MHz, CDCl3): δ 7.36 (d, J = 8.0 Hz, 2H), 7.10 (d, J = 8.0 Hz,
Thiobis(4,1-phenylene) diacetate(3s): after purification by silica gel
column chromatography (PE : EA = 5 : 1), compound 3s was isolated
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