PAPER
Synthesis of Sulfides from Aryl Disulfides and Alkyl Halides
91
1H NMR (300 MHz, CDCl3): d = 1.03 (t, J = 7.3 Hz, 3 H, CH3),
1.68 (m, 2 H, CH2), 2.91 (t, J = 7.2 Hz, 2 H, CH2), 7.17–7.20 (m,
1 H, Ar), 7.26–7.37 (m, 4 H, Ar).
(3) (a) Lindley, J. Tetrahedron 1984, 40, 1433. (b) Yunoki, S.
I.; Takimiya, K.; Aso, Y.; Otsubo, T. Tetrahedron Lett.
1997, 38, 3017. (c) Yin, J.; Pidgeon, C. Tetrahedron Lett.
1997, 38, 5953.
13C NMR (75 MHz, CDCl3): d = 14.3, 23.4, 36.5, 126.5, 129.6,
129.8, 137.8.
(4) Shah, S. T. A.; Khan, K. M.; Heinrich, A. M.; Voelter, W.
Tetrahedron Lett. 2002, 43, 8281.
Anal. Calcd for C9H12S: C, 71.00; H, 7.94. Found: C, 70.75; H,
7.76.
(5) (a) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992,
33, 8099. (b) Page, P. C. B.; Klair, S. S.; Brown, M. P.;
Harding, M. M.; Smith, C. S.; Maginn, S. J.; Mulley, S.
Tetrahedron Lett. 1998, 29, 4477. (c) Li, C.-J.; Harpp, D. N.
Tetrahedron Lett. 1992, 33, 7293.
1-(1-Methylethylthio)benzene (6u)
Colorless liquid.
(6) Chowdhury, S.; Roy, S. Tetrahedron Lett. 1997, 38, 2149.
(7) (a) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
(b) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org.
Lett. 2002, 4, 2803. (c) Taniguchi, N.; Onami, T. J. Org.
Chem. 2004, 69, 915.
(8) Ranu, B. C.; Mandal, T. J. Org. Chem. 2004, 69, 5793.
(9) Tang, R. Y.; Zhong, P.; Lin, Q. L. J. Fluorine Chem. 2006,
127, 948.
IR (KBr): 3056, 2962, 2923, 1582, 1475, 1439, 1382, 742, 692
cm–1.
1H NMR (300 MHz, CDCl3): d = 1.31 (d, J = 6.7 Hz, 6 H, CH3),
3.39 (m, 1 H, CH), 7.20–7.33 (m, 3 H, Ar), 7.40–7.43 (d, J = 7.7
Hz, 2 H, Ar).
13C NMR (75 MHz, CDCl3): d = 24.0, 39.1, 127.5, 129.6, 132.7,
136.4.
(10) (a) Wakselman, C.; Tordeux, M.; Clavel, J. L.; Langlois, B.
J. Chem. Soc., Chem. Commun. 1991, 993. (b) Clavel, J. L.;
Langlois, B.; Nantermet, R.; Tordeux, M.; Wakselman, C.
J. Chem. Soc., Perkin Trans. 1 1992, 3371.
(11) For reviews on the application of sodium dithionite in
organic synthesis, see: (a) Cho, J.; Sato, S.; Takeoka, S.;
Tsuchida, E. Macromolecules 2001, 34, 2751.
Anal. Calcd for C9H12S: C, 71.00; H, 7.94. Found: C, 70.78; H,
7.81.
1-Butylthiobenzene (6v)
Colorless liquid.7b
IR (KBr): 3058, 2957, 2928, 2869, 1582, 1478, 1438, 737, 689
cm–1.
(b) Overberger, C. G.; McGill, E. V.; Anselme, J. P. J. Am.
Chem. Soc. 1969, 91, 687. (c) Hawthorne, J. O.; Mihelic, E.
L.; Morgan, M. S.; Wilt, M. H. J. Org. Chem. 1963, 28,
2831. (d) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1.
(e) Haddadin, M. J.; Alkaysi, H. N.; Saheb, S. E.
Tetrahedron 1970, 26, 1115. (f) Brimble, M. A.; Nairn, M.
R. J. Chem. Soc., Perkin Trans. 1 2000, 317. (g) de Vries, J.
G.; Kellogg, R. M. J. Org. Chem. 1980, 45, 4126. (h) Cao,
P.; Duan, J. X.; Chen, Q. Y. J. Chem. Soc., Chem. Commun.
1994, 737. (i) Huang, W. Y.; Hu, L. Q.; Ge, W. Z.
J. Fluorine Chem. 1989, 43, 305. (j) Tang, X. Q.; Hu, C. M.
J. Chem. Soc., Chem. Commun. 1994, 631. (k) Tordeux,
M.; Langlois, B.; Wakselman, C. J. Chem. Soc., Perkin
Trans. 1 1990, 2293.
1H NMR (300 MHz, CDCl3): d = 0.93 (t, J = 7.3 Hz, 3 H, CH3),
1.45 (m, 2 H,CH2), 1.65 (m, 2 H, CH2), 2.93 (t, J = 7.3 Hz, 2 H,
CH2), 7.26–7.35 (m, 5 H, Ar).
13C NMR (75 MHz, CDCl3): d = 13.6, 21.9, 31.2, 33.2, 127.1,
128.9, 129.0, 137.0.
Anal. Calcd for C10H14S: C, 72.23; H, 8.49. Found: C, 71.98; H,
8.27.
1-Nitro-4-(phenylthiomethyl)benzene (6y)
Yellow solid; mp 70–71 °C.
IR (KBr): 2926, 2846, 1602, 1576, 1514, 1477, 1435, 858, 742
cm–1.
(12) For reviews on the application of sodium dithionite in
organic synthesis, see: (a) Beatriz, M. I.; Nazario, M.;
Carlos, S. J. Org. Chem. 1997, 62, 7585. (b) Liu, W. D.;
Chi, C. C.; Pai, I. F.; Wu, A. T.; Chung, W. S. J. Org. Chem.
2002, 67, 9267. (c) Liu, J. H.; Wu, A. T.; Huang, M. W.;
Wu, C. W.; Chung, W. S. J. Org. Chem. 2000, 65, 3395.
(d) Huang, B. N.; Liu, J. T.; Huang, W. Y. J. Chem. Soc.,
Perkin Trans. 1 1994, 101. (e) Huang, B. N.; Liu, J. T.
Tetrahedron Lett. 1990, 31, 2711. (f) Huang, B. N.; Liu, J.
T.; Huang, W. Y. J. Chem. Soc., Chem. Commun. 1990,
1781. (g) William, R. D.; Maurice, M.; Samia, A. M.
Tetrahedron Lett. 2001, 42, 4811. (h) Anselmi, E.;
Blazejewski, J. C.; Tordeux, M.; Wakselman, C. J. Fluorine
Chem. 2000, 105, 41. (i) Wu, F. H.; Huang, B. N.; Lu, L.;
Huang, W. Y. J. Fluorine Chem. 1996, 80, 91.
1H NMR (300 MHz, CDCl3): d = 4.14 (s, 2 H, CH2), 7.22–7.30 (m,
5 H, Ar), 7.39 (d, J = 8.6 Hz, 2 H, Ar), 8.12 (d, J = 8.6 Hz, 2 H, Ar).
13C NMR (75 MHz, CDCl3): d = 39.8, 124.5, 128.1, 129.9, 130.4,
131.9, 135.6, 146.4, 147.9.
Anal. Calcd for C13H11NO2S: C, 63.65; H, 4.52. Found: C, 63.37; H,
4.23.
Acknowledgment
Project supported by the National Natural Science Foundation of
China (No. 20572079) and the National Natural Science Foundation
of Zhejiang Province (No. Y205540 and Y404039). Supported by
the Wenzhou University Postgraduate Innovation Foundation (No.
YCX0514).
(13) Tang, R. Y.; Zhong, P.; Lin, Q. L. Phosphorus, Sulfur
Silicon Relat. Elem. 2006, in press.
(14) Antonello, S.; Daasbjerg, K.; Jensen, H.; Taddei, F.; Maran,
F. J. Am. Chem. Soc. 2003, 125, 14905.
References
(15) Antonello, S.; Benassi, R.; Gavioli, G.; Taddei, F.; Maran, F.
J. Am. Chem. Soc. 2002, 124, 7529.
(16) Hodgson, W. G.; Neaves, A.; Parker, C. A. Nature (London)
1956, 178, 489.
(17) Zheng, N.; McWilliams, J. C.; Fleitz, F. J.; Armstrong, J. D.
III; Volante, R. P. J. Org. Chem. 1998, 63, 9606.
(1) For general reviews on sulfides, see: Jones, D. N. In
Comprehensive Organic Chemistry, Vol. 3; Barton, D. H.
R.; Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979, 33–
103.
(2) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000,
2, 2019; and references therein.
Synthesis 2007, No. 1, 85–91 © Thieme Stuttgart · New York