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RSC Advances
DOI: 10.1039/C6RA12557C
ARTICLE
1,2-bis(3-nitrophenyl) disulfide (2e) : Yellow solid; yield:
RSC Advances
3
1
2.
K. Appelt, J. A. Burgess, K. M. Campanale, N. Y. Chirgadze,
D. K. Clawson, B. A. Dressman, S. D. Hatch, D. A. Khalil, M.
B. Kosa, P. P. Lubbehusen, M. A. Muesing, A. K. Patick, S. H.
Reich, K. S. Su and J. H. Tatlock, J. Med. Chem., 1997, 40,
3979–3985.
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0
–
2
3
.102 g (67%) mp 80-81°C; H NMR: (400 MHz, cdcl ) δ 8.36
8.31 (m, 2H), 8.07 (d, J = 7.2, 5.1 Hz, 2H), 7.85 – 7.76 (m,
H), 7.51 (d, J = 8.1 Hz, 2H); LC-MS m/z (% relative
intensity): 308.
3
G. Liu, J. R. Huth, E. T. Olejniczak, R. Mendoza, P. DeVries,
S. Leitza, E. B. Reilly, G. F. Okasinski, S. W. Fesik and T. W.
von Geldern, J. Med. Chem., 2001, 44, 1202–1210.
B. C. Ranu, A. Saha and R. Jana, Adv. Synth. Catal., 2007,
349, 2690–2696.
6
. 1,2-bis(4-nitrophenyl) disulfide (2f) : Yellow solid; yield:
1
3
1
.104 g (68%); mp 171-174°C; H NMR: (400 MHz, cdcl
0
3
) δ
7.46 – 7.35 (m, 4H), 7.26 (d, J = 7.3 Hz, 4H); LC-MS m/z (%
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7
8
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relative intensity): 308.
. 1, 2-bis (4-chlorophenyl) disulfide (2h) : White solid;
S. V Ley and A. W. Thomas, Angew. Chemie Int. Ed., 2003,
42, 5400–5449.
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0
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yield: 0.106 g (74%); mp 69-72°C; H NMR (400 MHz, cdcl
δ 7.46 – 7.35 (m, 4H), 7.26 (d, J = 7.3 Hz, 4H); GC-MS m/z
% relative intensity 286(M+, 65), 143(100), 251(5), 222(6),
08(62).
3
)
I. P. Beletskaya and A. V Cheprakov, Coord. Chem. Rev.,
2004, 248, 2337–2364.
(
C.-K. Chen, Y.-W. Chen, C.-H. Lin, H.-P. Lin and C.-F. Lee,
Chem. Commun., 2010, 46, 282–284.
1
M. Carril, R. SanMartin, E. Domínguez and I. Tellitu, Chem.
– A Eur. J., 2007, 13, 5100–5105.
4
5. Diphenyl sulphide (3a) : Yellow liquid; yield: 0.137 g
4
1
75%); H NMR (400 MHz, cdcl
(
3
) δ 7.36-7.22 (m, J = 7.6 Hz,
Z. Qiao and X. Jiang, Org. Lett., 2016, 18, 1550– 1553.
A. Habibi, M. H. Baghersad, M. Bilabary and Y. Valizadeh,
Tetrahedron Lett., 2016, 57, 559–562.
1
0H); GC-MS m/z (% relative intensity): 186(M+, 100), 152 10
(8), 77(10).
1
1
Y. Li, C. Nie, H. Wang, X. Li, F. Verpoort and C. Duan,
European J. Org. Chem., 2011, 7331–7338.
M. Soleiman-Beigi, I. Yavari and F. Sadeghizadeh, RSC Adv.,
2015, 5, 87564–87570.
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. Bis(4-methoxyphenyl) sulphide (3c) : Yellow solid; yield:
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1
0
.177 g (72%); mp 46-47°C; H NMR (400 MHz, cdcl
d, J = 8.8 Hz, 4H), 6.81 (d, J = 8.7 Hz, 4H), 3.77 (s, 6H); GC-
MS m/z (% relative intensity): 246(M+, 100), 231 (40), 13
28(7), 203(11).
3
) δ 7.25 12
(
R. K. Sharma, R. Gaur, M. Yadav, A. K. Rathi, J. Pechousek,
M. Petr, R. Zboril and M. B. Gawande, ChemCatChem,
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2
015, 7, 3495–3502.
1
Bis(2-methylphenyl) sulphide (3d) : White solid; yield: 14
1
7.
A. Rostami, A. Rostami, N. Iranpoor and M. A. Zolfigol,
Tetrahedron Lett., 2016, 57, 192–195.
1
0
–
7
3
.142 g (68%); mp 63-65°C; H NMR (400 MHz, cdcl ) δ 7.25
7.20 (m, 2H), 7.19 – 7.12 (m, 2H), 7.10 (d, J = 7.8 Hz, 2H), 15
.05 (t, J = 6.7 Hz, 2H), 2.37 (s, 6H); GC-MS m/z (% relative
M. A. Fernández-Rodríguez, Q. Shen and J. F. Hartwig, J.
Am. Chem. Soc., 2006, 128, 2180–2181.
G. Bastug and S. P. Nolan, J. Org. Chem., 2013, 78, 9303–
9308.
intensity): 214(M+, 100), 199(11), 184(6), 153(2),122(33), 16
05(10), 91(13).
1
1
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M. A. Fernández-Rodríguez and J. F. Hartwig, J. Org. Chem.,
2009, 74, 1663–1672.
4
8. Bis(3-nitrophenyl) sulphide (3e) : Yellow solid; yield:
4
1
.174 g (63%); mp 57-60°C; H NMR : (400 MHz, cdcl
0
8
7
3
) δ 18
Y.-C. Wong, T. T. Jayanth and C.-H. Cheng, Org. Lett., 2006,
8, 5613–5616.
.18 (s, 2H), 8.15 (d, J = 8.2 Hz, 2H), 7.68 – 7.63 (m, 2H),
.53 (t, J = 8.0 Hz, 2H).
19
V. Percec, J.-Y. Bae and D. H. Hill, J. Org. Chem., 1995, 60,
6
895–6903.
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4
Bis(4-bromophenyl) sulphide (3i) : White solid; yield: 0.24 20
9.
G. B. B. Varadwaj, S. Rana and K. M. Parida, RSC Adv., 2013,
3, 7570–7578.
1
3
g (71%); mp 112-114°C; H NMR: (400 MHz, cdcl ) δ 7.41 (d,
J = 8.5 Hz, 4H), 7.16 (d, J = 8.5 Hz, 4H); GC-MS m/z (% 21
Y. Zhang, K. C. Ngeow and J. Y. Ying, Org. Lett., 2007, 9,
3495–3498.
relative intensity): 344(M+, 100), 342(35), 267(33), 183(14),
155(20), 77(20).
22
M. Soleiman-Beigi and Z. Arzehgar, Heteroat. Chem., 2015,
2
6, 355–360.
L.-B. Han and M. Tanaka, J. Am. Chem. Soc., 1998, 120,
249–8250.
J.-R. Wu, C.-H. Lin and C.-F. Lee, Chem. Commun., 2009,
450–4452.
V. K. Akkilagunta, V. P. Reddy and K. R. Rao, Synlett, 2010,
010, 1260–1264.
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Acknowledgments
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The authors are thankful to UGC-SAP New Delhi (India) for
providing financial assistance and Dr. Vinod Parab Loba
chemie, India for providing a gift samples.
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C.-S. Lai, H.-L. Kao, Y.-J. Wang and C.-F. Lee, Tetrahedron
Lett., 2012, 53, 4365–4367.
Notes and references
V. P. Reddy, A. V. Kumar, K. Swapna and K. R. Rao, Org.
Lett., 2009, 11, 1697–1700.
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X. Lv and W. Bao, J. Org. Chem., 2007, 72, 3863–3867.
S. W. Kaldor, V. J. Kalish, J. F. Davies, B. V Shetty, J. E. Fritz,
V. P. Reddy, K. Swapna, A. V. Kumar and K. R. Rao, J. Org.
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| J. Name., 2012, 00, 1-3
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