Preparation of a new 1,2,3-trithiolane, trans-9,10,11-trithiabicyclo[6.3.0]undecane, and its oxidation reactions

Tetrahedron

Volumn 62, Issue 23, 2006, Pages 5441-5447

  Ishii, Akihiko ^a   Suzuki, Manami ^a   Yamashita, Remi ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

Cyclooctene; Isomerization; Octasulfur monoxide; Oxidation; Trithiolane

Indexed keywords

1,2,3 TRITHIOLANE; 9,10,11 TRITHIABICYCLO[6.3.0]UNDECANE; 9,10,11 TRITHIABICYCLO[6.3.0]UNDECANE 10 OXIDE; 9,10,11 TRITHIABICYCLO[6.3.0]UNDECANE 9 OXIDE; 9,10,11 TRITHIABICYCLO[6.3.0]UNDECANE 9,11 DIOXIDE; 9,10,11 TRITHIABICYLO[6.3.0]UNDECANE 9,11 DIOXIDE; DECANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ISOMERIZATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 33748081451     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.03.044     Document Type: Article

References (48)

1. Mitchell G. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 4 (1996), Pergamon, Oxford 545-580 Chapter 4.15
2. Steudel R. Chem. Rev. (2002) 3905-3945
3. Krespan C.G., and Brasen W.R. J. Org. Chem. 27 (1962) 3995-4000
4. Shields T.C., and Kurtz A.N. J. Am. Chem. Soc. 91 (1969) 5415-5416
5. Kurz, A. N.; Shields, T. C. U.S. Patent 3586700 19710622 (CAN 75:89064), 1971.
6. Emsley J., Griffiths D.W., and Jayne G.J.J. J. Chem. Soc., Perkin Trans. 1 (1979) 228-232
7. Inoue S., Tezuka T., and Oae S. Phosphorus Sulfur 4 (1978) 219-221
8. Bartlett P.D., and Ghosh T. J. Org. Chem. 52 (1987) 4937-4943
9. Steliou K., Gareau Y., Milot G., and Salama P. J. Am. Chem. Soc. 112 (1990) 7819-7820
10. Nakayama J., Ito Y., and Mizumura A. Sulfur Lett. 14 (1992) 247-250
11. Gilchrist T.L., and Wood J.E. J. Chem. Soc., Chem. Commun. (1992) 1460-1461
12. Sato R., Satoh S., and Saito M. Chem. Lett. (1990) 139-142
13. Ishii A., Nakabayashi M., and Nakayama J. J. Am. Chem. Soc. 121 (1999) 7959-7960
14. Ishii A., Nakabayashi M., Jin Y.-N., and Nakayama J. J. Organomet. Chem. 611 (2000) 127-135
15. Nakayama J., Aoki S., Takayama J., Sakamoto A., Sugihara Y., and Ishii A. J. Am. Chem. Soc. 126 (2004) 9085-9093
16. Hamid A.M., and Trippett S. J. Chem. Soc. C (1968) 1612-1615
17. Ghosh T., and Bartlett P.D. J. Am. Chem. Soc. 110 (1988) 7499-7506
18. Block E., Iyer R., Grisoni S., Saha C., Belman S., and Lossing F.P. J. Am. Chem. Soc. 110 (1988) 7813-7827
19. Steudel R., Kustos M., Münchow V., and Westphal U. Chem. Ber. Recl. 130 (1997) 757-764
20. Sugihara Y., Abe K., and Nakayama J. Heteroat. Chem. 10 (1999) 638-643
21. Lacombe S.M. Rev. Heteroat. Chem. 21 (1999) 1-41
22. Clennan E.L., and Stensaas K.L. Org. Prep. Proced. Int. 30 (1998) 551-600
23. Derbesy G., and Harpp D.N. Sulfur Rep. 16 (1995) 363-369
24. Ishii A., Oshida H., and Nakayama J. Bull. Chem. Soc. Jpn. 75 (2002) 319-328
25. Ishii A., Oshida H., and Nakayama J. Tetrahedron Lett. 42 (2001) 3117-3119
26. Adam W., Bargon R.M., and Mloston G. Eur. J. Org. Chem. (2003) 4012-4015
27. Adam W., and Bargon R.M. Chem. Commun. (2001) 1910-1911
28. Adam W., Bargon R.M., and Schenk W.A. J. Am. Chem. Soc. 125 (2003) 3871-3876
29. Adam W., and Fröhling B. Org. Lett. 4 (2002) 599-602
30. Adam W., and Weinkötz S. J. Am. Chem. Soc. 120 (1998) 4861-4862
31. Ishii A., Kawai T., Tekura K., Oshida H., and Nakayama J. Angew. Chem., Int. Ed. 40 (2001) 1924-1926
32. Steudel R., and Latte J. Angew. Chem., Int. Ed. Engl. 13 (1974) 603-604
33. Watson W.H., Krawiec M., Ghosh T., and Bartlett P.D. Acta Crystallogr. C48 (1992) 2092-2094
34. Satoh S., and Sato R. Bull. Chem. Soc. Jpn. 65 (1992) 1188-1190
35. Inoue Y., Tsuneishi H., Hakushi T., and Tai A. In: Mattay J., and Griesbeck A. (Eds). Photochemical Key Steps in Organic Synthesis: An Experimental Course Book (1994), VCH, Weinheim 207
36. Inoue Y., Takamuku S., and Sakurai H. Synthesis (1976) 111
37. Adam W., Bialas J., and Hadjiarapoglou L. Chem. Ber. 124 (1991) 2377
38. Adam W., Hadjiarapoglou L., and Smerz A. Chem. Ber. 124 (1991) 227-232
39. Eliel E.L., Wilen S.H., and Doyle M.P. Basic Organic Stereochemistry (2001), Wiley, New York, NY p 487
40. Ishii A., Nakamura S., Yamada T., and Nakayama J. Tetrahedron 53 (1997) 12203-12214
41. Ishii A., Kawai T., Noji M., and Nakayama J. Tetrahedron 61 (2005) 6693-6699
42. Nakayama J., and Ishii A. Adv. Heterocycl. Chem. 77 (2000) 221-284
43. Nicolaou K.C., Hwang C.-K., Duggan M.E., and Carroll P.J. J. Am. Chem. Soc. 109 (1987) 3801-3802
44. Ishii A., Kashiura S., Oshida H., and Nakayama J. Org. Lett. 6 (2004) 2623-2626
45. Blessing R.H. Acta Crystallogr. A51 (1995) 33-38
46. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., and Spagna R. J. Appl. Crystallogr. 32 (1999) 115-119
47. Sheldrick G.M. SHELXL-97, Program for Crystal Structure Refinement (1997), Göttingen University, Germany
48. North A.C.T., Phillips D.C., and Mathews F.S. Acta Crystallogr. A24 (1968) 351-359