Selective synthesis of organic sulfides and disulfides by the reduction of elemental sulfur with samarium diiodide

Heteroatom Chemistry

Volumn 9, Issue 6, 1998, Pages 581-584

  Ogawa, Akiya ^a   Takami, Noriaki ^a   Sekiguchi, Masahito ^a   Sonoda, Noboru ^b   Hirao, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011233098     PISSN: 10427163     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1071(1998)9:6<581::AID-HC9>3.0.CO;2-7     Document Type: Article

References (42)

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6. 2, see (a) H. B. Kagan, J. L. Namy, Tetrahedron, 42, 1986, 6573; (b) H. B. Kagan, New J. Chem., 14, 1990, 453; (c) G. A. Molander: in B. M. Trost (ed): Comprehensive Organic Synthesis, Pergamon Press, Oxford, vol. 1, chap. 1.9, p. 251 (1991), (d) J. A. Soderquist, Aldrich. Acta, 24, 1991, 15; (e) G. A. Molander, Chem. Rev., 92, 1992, 29; (f) G. A. Molander, Org. React., 46, 1994, 211; (g) T. Imamoto: Lanthanides in Organic Synthesis, Academic Press, New York, pp. 21-62 (1994); (h) G. A. Molander, C. R. Harris, Chem. Rev., 96, 1996, 307.
7. 2, see (a) H. B. Kagan, J. L. Namy, Tetrahedron, 42, 1986, 6573; (b) H. B. Kagan, New J. Chem., 14, 1990, 453; (c) G. A. Molander: in B. M. Trost (ed): Comprehensive Organic Synthesis, Pergamon Press, Oxford, vol. 1, chap. 1.9, p. 251 (1991), (d) J. A. Soderquist, Aldrich. Acta, 24, 1991, 15; (e) G. A. Molander, Chem. Rev., 92, 1992, 29; (f) G. A. Molander, Org. React., 46, 1994, 211; (g) T. Imamoto: Lanthanides in Organic Synthesis, Academic Press, New York, pp. 21-62 (1994); (h) G. A. Molander, C. R. Harris, Chem. Rev., 96, 1996, 307.
8. 2, see (a) H. B. Kagan, J. L. Namy, Tetrahedron, 42, 1986, 6573; (b) H. B. Kagan, New J. Chem., 14, 1990, 453; (c) G. A. Molander: in B. M. Trost (ed): Comprehensive Organic Synthesis, Pergamon Press, Oxford, vol. 1, chap. 1.9, p. 251 (1991), (d) J. A. Soderquist, Aldrich. Acta, 24, 1991, 15; (e) G. A. Molander, Chem. Rev., 92, 1992, 29; (f) G. A. Molander, Org. React., 46, 1994, 211; (g) T. Imamoto: Lanthanides in Organic Synthesis, Academic Press, New York, pp. 21-62 (1994); (h) G. A. Molander, C. R. Harris, Chem. Rev., 96, 1996, 307.
9. 2, see (a) H. B. Kagan, J. L. Namy, Tetrahedron, 42, 1986, 6573; (b) H. B. Kagan, New J. Chem., 14, 1990, 453; (c) G. A. Molander: in B. M. Trost (ed): Comprehensive Organic Synthesis, Pergamon Press, Oxford, vol. 1, chap. 1.9, p. 251 (1991), (d) J. A. Soderquist, Aldrich. Acta, 24, 1991, 15; (e) G. A. Molander, Chem. Rev., 92, 1992, 29; (f) G. A. Molander, Org. React., 46, 1994, 211; (g) T. Imamoto: Lanthanides in Organic Synthesis, Academic Press, New York, pp. 21-62 (1994); (h) G. A. Molander, C. R. Harris, Chem. Rev., 96, 1996, 307.
10. 2, see (a) H. B. Kagan, J. L. Namy, Tetrahedron, 42, 1986, 6573; (b) H. B. Kagan, New J. Chem., 14, 1990, 453; (c) G. A. Molander: in B. M. Trost (ed): Comprehensive Organic Synthesis, Pergamon Press, Oxford, vol. 1, chap. 1.9, p. 251 (1991), (d) J. A. Soderquist, Aldrich. Acta, 24, 1991, 15; (e) G. A. Molander, Chem. Rev., 92, 1992, 29; (f) G. A. Molander, Org. React., 46, 1994, 211; (g) T. Imamoto: Lanthanides in Organic Synthesis, Academic Press, New York, pp. 21-62 (1994); (h) G. A. Molander, C. R. Harris, Chem. Rev., 96, 1996, 307.
11. 2, see (a) H. B. Kagan, J. L. Namy, Tetrahedron, 42, 1986, 6573; (b) H. B. Kagan, New J. Chem., 14, 1990, 453; (c) G. A. Molander: in B. M. Trost (ed): Comprehensive Organic Synthesis, Pergamon Press, Oxford, vol. 1, chap. 1.9, p. 251 (1991), (d) J. A. Soderquist, Aldrich. Acta, 24, 1991, 15; (e) G. A. Molander, Chem. Rev., 92, 1992, 29; (f) G. A. Molander, Org. React., 46, 1994, 211; (g) T. Imamoto: Lanthanides in Organic Synthesis, Academic Press, New York, pp. 21-62 (1994); (h) G. A. Molander, C. R. Harris, Chem. Rev., 96, 1996, 307.
12. 2, see (a) H. B. Kagan, J. L. Namy, Tetrahedron, 42, 1986, 6573; (b) H. B. Kagan, New J. Chem., 14, 1990, 453; (c) G. A. Molander: in B. M. Trost (ed): Comprehensive Organic Synthesis, Pergamon Press, Oxford, vol. 1, chap. 1.9, p. 251 (1991), (d) J. A. Soderquist, Aldrich. Acta, 24, 1991, 15; (e) G. A. Molander, Chem. Rev., 92, 1992, 29; (f) G. A. Molander, Org. React., 46, 1994, 211; (g) T. Imamoto: Lanthanides in Organic Synthesis, Academic Press, New York, pp. 21-62 (1994); (h) G. A. Molander, C. R. Harris, Chem. Rev., 96, 1996, 307.
13. M. Sekiguchi, H. Tanaka, N. Takami, A. Ogawa, I. Ryu, N. Sonoda, Heteroat. Chem., 2, 1991, 427.
14. 2-induced reduction of organic sulfur compounds such as sulfoxides, vinylic sulfides, thiocyanates, etc., see for example, (a) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun., 1989, 298; (b) T. Kataoka, T. Iwama, K. Tsutsumi, Y. Nakamura, H. Matsumoto, H. Shimizu, M. Hori, J. Chem. Res., Synop., 1992, 393; (c) M. Hojo, H. Harada, J. Yoshizawa, A. Hosomi, J. Org. Chem., 58, 1993, 6541; (d) X. Jia, Y. Zhang, X. Zhou, Tetrahedron Lett., 35, 1994, 8833; (e) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 387; (f) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 2893; (g) I. W. J. Still, T. F. Dean, J. Org. Chem., 61, 1996, 7677; (h) H. Guo, J. Wang, Y. Zhang, Synth. Commun., 27, 1997, 85; (i) Y. Huang, Y. Zhang, Y. Wang, Synth. Commun., 27, 1997, 1043.
15. 2-induced reduction of organic sulfur compounds such as sulfoxides, vinylic sulfides, thiocyanates, etc., see for example, (a) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun., 1989, 298; (b) T. Kataoka, T. Iwama, K. Tsutsumi, Y. Nakamura, H. Matsumoto, H. Shimizu, M. Hori, J. Chem. Res., Synop., 1992, 393; (c) M. Hojo, H. Harada, J. Yoshizawa, A. Hosomi, J. Org. Chem., 58, 1993, 6541; (d) X. Jia, Y. Zhang, X. Zhou, Tetrahedron Lett., 35, 1994, 8833; (e) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 387; (f) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 2893; (g) I. W. J. Still, T. F. Dean, J. Org. Chem., 61, 1996, 7677; (h) H. Guo, J. Wang, Y. Zhang, Synth. Commun., 27, 1997, 85; (i) Y. Huang, Y. Zhang, Y. Wang, Synth. Commun., 27, 1997, 1043.
16. 2-induced reduction of organic sulfur compounds such as sulfoxides, vinylic sulfides, thiocyanates, etc., see for example, (a) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun., 1989, 298; (b) T. Kataoka, T. Iwama, K. Tsutsumi, Y. Nakamura, H. Matsumoto, H. Shimizu, M. Hori, J. Chem. Res., Synop., 1992, 393; (c) M. Hojo, H. Harada, J. Yoshizawa, A. Hosomi, J. Org. Chem., 58, 1993, 6541; (d) X. Jia, Y. Zhang, X. Zhou, Tetrahedron Lett., 35, 1994, 8833; (e) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 387; (f) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 2893; (g) I. W. J. Still, T. F. Dean, J. Org. Chem., 61, 1996, 7677; (h) H. Guo, J. Wang, Y. Zhang, Synth. Commun., 27, 1997, 85; (i) Y. Huang, Y. Zhang, Y. Wang, Synth. Commun., 27, 1997, 1043.
17. 2-induced reduction of organic sulfur compounds such as sulfoxides, vinylic sulfides, thiocyanates, etc., see for example, (a) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun., 1989, 298; (b) T. Kataoka, T. Iwama, K. Tsutsumi, Y. Nakamura, H. Matsumoto, H. Shimizu, M. Hori, J. Chem. Res., Synop., 1992, 393; (c) M. Hojo, H. Harada, J. Yoshizawa, A. Hosomi, J. Org. Chem., 58, 1993, 6541; (d) X. Jia, Y. Zhang, X. Zhou, Tetrahedron Lett., 35, 1994, 8833; (e) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 387; (f) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 2893; (g) I. W. J. Still, T. F. Dean, J. Org. Chem., 61, 1996, 7677; (h) H. Guo, J. Wang, Y. Zhang, Synth. Commun., 27, 1997, 85; (i) Y. Huang, Y. Zhang, Y. Wang, Synth. Commun., 27, 1997, 1043.
18. 2-induced reduction of organic sulfur compounds such as sulfoxides, vinylic sulfides, thiocyanates, etc., see for example, (a) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun., 1989, 298; (b) T. Kataoka, T. Iwama, K. Tsutsumi, Y. Nakamura, H. Matsumoto, H. Shimizu, M. Hori, J. Chem. Res., Synop., 1992, 393; (c) M. Hojo, H. Harada, J. Yoshizawa, A. Hosomi, J. Org. Chem., 58, 1993, 6541; (d) X. Jia, Y. Zhang, X. Zhou, Tetrahedron Lett., 35, 1994, 8833; (e) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 387; (f) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 2893; (g) I. W. J. Still, T. F. Dean, J. Org. Chem., 61, 1996, 7677; (h) H. Guo, J. Wang, Y. Zhang, Synth. Commun., 27, 1997, 85; (i) Y. Huang, Y. Zhang, Y. Wang, Synth. Commun., 27, 1997, 1043.
19. 2-induced reduction of organic sulfur compounds such as sulfoxides, vinylic sulfides, thiocyanates, etc., see for example, (a) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun., 1989, 298; (b) T. Kataoka, T. Iwama, K. Tsutsumi, Y. Nakamura, H. Matsumoto, H. Shimizu, M. Hori, J. Chem. Res., Synop., 1992, 393; (c) M. Hojo, H. Harada, J. Yoshizawa, A. Hosomi, J. Org. Chem., 58, 1993, 6541; (d) X. Jia, Y. Zhang, X. Zhou, Tetrahedron Lett., 35, 1994, 8833; (e) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 387; (f) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 2893; (g) I. W. J. Still, T. F. Dean, J. Org. Chem., 61, 1996, 7677; (h) H. Guo, J. Wang, Y. Zhang, Synth. Commun., 27, 1997, 85; (i) Y. Huang, Y. Zhang, Y. Wang, Synth. Commun., 27, 1997, 1043.
20. 2-induced reduction of organic sulfur compounds such as sulfoxides, vinylic sulfides, thiocyanates, etc., see for example, (a) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun., 1989, 298; (b) T. Kataoka, T. Iwama, K. Tsutsumi, Y. Nakamura, H. Matsumoto, H. Shimizu, M. Hori, J. Chem. Res., Synop., 1992, 393; (c) M. Hojo, H. Harada, J. Yoshizawa, A. Hosomi, J. Org. Chem., 58, 1993, 6541; (d) X. Jia, Y. Zhang, X. Zhou, Tetrahedron Lett., 35, 1994, 8833; (e) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 387; (f) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 2893; (g) I. W. J. Still, T. F. Dean, J. Org. Chem., 61, 1996, 7677; (h) H. Guo, J. Wang, Y. Zhang, Synth. Commun., 27, 1997, 85; (i) Y. Huang, Y. Zhang, Y. Wang, Synth. Commun., 27, 1997, 1043.
21. 2-induced reduction of organic sulfur compounds such as sulfoxides, vinylic sulfides, thiocyanates, etc., see for example, (a) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun., 1989, 298; (b) T. Kataoka, T. Iwama, K. Tsutsumi, Y. Nakamura, H. Matsumoto, H. Shimizu, M. Hori, J. Chem. Res., Synop., 1992, 393; (c) M. Hojo, H. Harada, J. Yoshizawa, A. Hosomi, J. Org. Chem., 58, 1993, 6541; (d) X. Jia, Y. Zhang, X. Zhou, Tetrahedron Lett., 35, 1994, 8833; (e) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 387; (f) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 2893; (g) I. W. J. Still, T. F. Dean, J. Org. Chem., 61, 1996, 7677; (h) H. Guo, J. Wang, Y. Zhang, Synth. Commun., 27, 1997, 85; (i) Y. Huang, Y. Zhang, Y. Wang, Synth. Commun., 27, 1997, 1043.
22. 2-induced reduction of organic sulfur compounds such as sulfoxides, vinylic sulfides, thiocyanates, etc., see for example, (a) Y. Handa, J. Inanaga, M. Yamaguchi, J. Chem. Soc. Chem. Commun., 1989, 298; (b) T. Kataoka, T. Iwama, K. Tsutsumi, Y. Nakamura, H. Matsumoto, H. Shimizu, M. Hori, J. Chem. Res., Synop., 1992, 393; (c) M. Hojo, H. Harada, J. Yoshizawa, A. Hosomi, J. Org. Chem., 58, 1993, 6541; (d) X. Jia, Y. Zhang, X. Zhou, Tetrahedron Lett., 35, 1994, 8833; (e) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 387; (f) X. Jia, Y. Zhang, X. Zhou, Synth. Commun., 24, 1994, 2893; (g) I. W. J. Still, T. F. Dean, J. Org. Chem., 61, 1996, 7677; (h) H. Guo, J. Wang, Y. Zhang, Synth. Commun., 27, 1997, 85; (i) Y. Huang, Y. Zhang, Y. Wang, Synth. Commun., 27, 1997, 1043.
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