Oxidation and reduction reactions of cis-9,10,11-trithiabicyclo[6.3.0] undecane synthesized by reaction of cis-Cyclooctene with S8O

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 184, Issue 5, 2009, Pages 1184-1205

  Ishii, Akihiko ^a   Suzuki, Manami ^a   Sone, Taeko ^a   Nakata, Norio ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

1,2,3 trithiolane; 1,2 dithiol; Cyclooctene; Oxidation; Reduction; Sulfuration

Indexed keywords

EID: 70349755654     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500902855232     Document Type: Article

References (38)

1. C. G. Krespan and W. R. Brasen, J. Org. Chem., 27, 3995 (1962);
2. T. C. Shields and A. N. Kurtz, J. Am. Chem. Soc., 91, 5415 (1961);
3. A. N. Kurz and T. C. Shields, US Patent (1971) 3586700 19710622 (CAN 75:89064);
4. J. Emsley, D. W. Griffiths, and G. J. J. Jayne, J. Chem. Soc., Perkin Trans. 1, 228 (1979);
5. S. Inoue, T. Tezuka, and S. Oae, Phosphorus Sulfur, 4, 219 (1978);
6. P. D. Bartlett and T. Ghosh, J. Org. Chem., 52, 4937 (1987);
7. K. Steliou, Y. Gareau, G. Milot, and P. Salama, J. Am . Chem. Soc., 112, 7819 (1990);
8. J. Nakayama, Y. Ito, and A. Mizumura, Sulfur Lett., 14, 247 (1992);
9. T. L. Gilchrist and J. E. Wood, J. Chem. Soc., Chem. Commun., 1460 (1992);
10. R. Sato, S. Satoh, and M. Saito, Chem. Lett., 139 (1990).
11. A. Ishii, M. Nakabayashi, and J. Nakayama, J. Am . Chem. S o c. , 121, 7959 (1999);
12. A. Ishii, M. Nakabayashi, Y.-N. Jin, and J. Nakayama, J. Organomet. Chem., 611, 127 (2000);
13. J. Nakayama, S. Aoki, J. Takayama, A. Sakamoto, Y. Sugihara, and A. Ishii, J. Am. Chem. Soc., 126, 9085 (2004).
14. W. Adam, R. M. Bargon, and G. Mloston, Eur. J. Org. Chem., 4012 (2003);
15. W. Adam and R. M. Bargon, Chem. Commun., 1910 (2001);
16. W. Adam, R. M. Bargon, and W. A. Schenk, J. Am . Chem. Soc. , 125, 3871 (2003);
17. W. Adam and B. Fröhling, Org. Lett., 4, 599 (2002);
18. W. Adam and S. Weinkötz, J. Am. Chem. Soc., 120, 4861 (1998).
19. A. Ishii, T. Kawai, K. Tekura, H. Oshida, and J. Nakayama, Angew. Chem. Int. Ed., 40, 1924 (2001).
20. R. Steudel and J. Latte, Angew. Chem. Int. Ed. Engl., 13, 603 (1974).
21. A. Ishii, M. Suzuki, and R. Yamashita, Tetrahedron, 62, 5441 (2006).
22. G. Mitchell, In: Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees, E. F. V. Scriven, Eds. (Pergamon, Oxford, 1996), Vol.4, Chap. 4.15, pp. 545-580;
23. R. Steudel, Chem. Rev., 3905 (2002).
24. M. Helgaker, M. Jaszuński, and K. Ruud, Chem. Rev., 99, 293 (1999);
25. A. Bango, Chem. Eur. J., 7, 1652 (2001).
26. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Mo-rokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian 03, Revision B.04, Gaussian, Inc., Pittsburgh, PA (2003).
27. [10] (a) F. Freeman, Chem. Rev., 84, 117 (1984);
28. E. L. Clenann and K. L. Stensaas, Org. Prep. Proced. Int., 30, 551 (1998);
29. S. Lacombe, In: Reviews on Heteroatom Chemistry, S. Oae, Ed. (Myu, Tokyo, 1999), Vol.21, pp. 1-41.
30. H. Oshida, A. Ishii, and J. Nakayama, Tetrahedron Lett., 43, 5033 (2002);
31. H. Oshida, A. Ishii, and J. Nakayama, J. Org. Chem., 69, 1695 (2004);
32. A. Ishii, S. Kashiura, H. Oshida, and J. Nakayama, Org. Lett., 6, 2623 (2004);
33. A. Ishii, M. Ohishi, K. Matsumoto, and T. Takayanagi, Org. Lett., 8, 91 (2006);
34. A. Ishii, J. Synth. Org. Jpn., 64, 395 (2006).
35. A. Ishii, K. Komiya, and J. Nakayama, J. Am . Chem. Soc., 118, 12836 (1996).
36. E. L. Eliel, S. H. Wilen, and M. P. Doyle, Basic Organic Stereochemistry (Wiley-Interscience, New York, 2001), p. 487.
37. W. Adam, J. Bialas, and L. Hadjiarapoglou, Chem. Ber., 124, 2377 (1991);
38. W. Adam, L. Hadjiarapoglou, and A. Smerz, Chem. Ber., 124, 227 (1991).