Synthesis and properties of three-membered cyclic bisulfides, dithiiranes

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 55, Issue 10, 1997, Pages 897-906

  Ishii, Akihiko ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

Absolute configuration; Bicyclic 1,3 dithietane; Dithiirane; Dithiirane 1 oxide; Optical resolution; Oxidative hydrolysis; OXONE; Oxygen migration; Thiosulfine; X ray analysis

Indexed keywords

EID: 0000105394     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.55.897     Document Type: Article

References (64)

1. K.C. Nicolaou, C.-K. Hwang, M.E. Duggan, P.J. Carroll, J. Am. Chem. Soc., 109, 3801 (1987);
2. K.C. Nicolaou, S.A. DeFrees, C.-K. Hwang, N. Stylianides, P.J. Carroll, J.P. Snyder, J. Am. Chem. Soc., ibid., 112, 3029 (1990)
3. E. Block, A.A. Bazzi, L.K. Revelle, J. Am. Chem. Soc., 102, 2490 (1980)
4. A. Ishii, Y.-N. Jin, Y. Sugihara, J. Nakayama, J. Chem. Soc., Chem. Commun., 1996, 2681;
5. Y.-N. Jin, A. Ishii, Y. Sugihara, J. Nakayama, Heterocycles, 44, 255 (1997)
6. F. Fehér, B. Degen, B. Söhngen, Angew. Chem., Int. Ed. Engl., 7, 301 (1968);
7. F. Fehér, J. Lex, Z. Anorg. Allg. Chem., 423, 103 (1976);
8. F. Fehér, K. Glinka, Z. Naturforsch., 34b, 1031 (1979);
9. N. Tokitoh, N. Takeda, R. Okazaki, J. Am. Chem. Soc., 116, 7907 (1994);
10. N. Takeda, N. Tokitoh, T. Imakubo, M. Goto, R. Okazaki, Bull. Chem. Soc. Jpn., 68, 2757 (1995)
11. K. Morita, S. Kobayashi, Chem. Pharm. Bull., 15, 988 (1967);
12. F. Fehér, J. Lex, K.-H. Linke, Z. Naturforsch., 24b, 1485 (1969);
13. R. Okazaki, K. Inoue, N. Inamoto, Bull. Chem. Soc. Jpn., 54, 3541 (1981)
14. F. Fehér, W. Becher, Z. Naturforsch., 20b, 1125 (1965);
15. W. Lutz, T. Pilling, G. Rihs, H. R. Waespe, T. Winkler, Tetrahedron Lett., 31, 5457 (1990);
16. F.W. Heinemann, H. Hartung, N. Maier, H. Matschiner, Z. Naturforsch., 49b, 1063 (1994)
17. N. Tokitoh, N. Takeda, T. Imakubo, M. Goto, R. Okazaki, Chem. Lett., 1992, 1599
18. A. Senning, H.C. Hansen, M.F. Abdel-Megeed, W. Mazurkiewicz, B. Jensen, Tetrahedron, 42, 739 (1986);
19. A. Senning, Sulfur Lett., 4, 213 (1986);
20. A. Senning, Sulfur Lett., idem. ibid., 11, 83 (1990)
21. R.W. Murray, Chem. Rev., 89, 1187 (1989);
22. W. Adam, R. Curci, J.O. Edwards, Acc. Chem. Res., 22, 205 (1989);
23. J.O. Edwards, R. H. Pater, R. Curci, F. DiFuria, Photochem. Photobiol., 30, 63 (1979)
24. J.P. Snyder, L. Carlsen, J. Am. Chem. Soc., 99, 2931 (1977)
25. R. Huisgen, G. Mloston, K. Polborn, F. Palacios-Gambra, Liebigs Ann. /Recueil, 1997, 187;
26. R. Huisgen, J. Rapp, J. Am. Chem. Soc., 109, 902 (1987)
27. A. Ishii, J. Nakayama, M.-X. Ding, N. Kotaka, M. Hoshino, J. Org. Chem., 55, 2421 (1990)
28. A. Ishii, M.-X. Ding, K. Maeda, J. Nakayama, M. Hoshino, Bull. Chem. Soc. Jpn., 65, 3343 (1992)
29. A. Ishii, T. Akazawa, M.-X. Ding, T. Honjo, J. Nakayama, H. Hoshino, M. Shiro, J. Am. Chem. Soc., 115, 4914 (1993)
30. A. Ishii, T. Akazawa, T. Maruta, J. Nakayama, M. Hoshino, M. Shiro, Angew. Chem., Int. Ed. Engl., 33, 777 (1994)
31. A. Ishii, S. Nakamura, T. Yamada, J. Nakayama, Tetrahedron, in press
32. OXONE® R.J. Kennedy, A.M. Stock, J. Org. Chem., 25, 1901 (1960);
33. B.M. Trost, D.P. Curran, Tetrahedron Lett., 22, 1287 (1981)
34. A. Ishii, T.Akazawa, M.-X. Ding, T. Honjo, T. Maruta, S. Nakamura, H. Nagaya, M. Ogura, K. Teramoto, M. Shiro, M. Hoshino, J. Nakayama, Bull. Chem. Soc. Jpn., 70, 509 (1997)
35. F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. II, 1987, S1
36. K. Okiya, C. Hirose, D.G. Lister, J. Sheridan, Chem. Phys. Lett.. 24, 111 (1974)
37. J.-G. Gourcy, G. Jeminet, J. Simonet, J. Chem. Soc., Chem. Commun., 1974, 634;
38. Q.N. Porter, J.H.P. Utley, J. Chem. Soc., Chem. Commun., ibid., 1978, 255;
39. D. Ghiringhelli, Synthesis, 1982, 580;
40. L. Mathew, S. Sankararaman, J. Org. Chem., 58, 7576 (1993);
41. K. Tanemura, H. Dohya, M. Imamura, T. Suzuki, T. Horaguchi, Chem. Lett., 1994, 965
42. G.A. Olah, S.C. Narang, G.F. Salem, Synthesis, 1980, 657
43. A. Ishii, T. Maruta, K. Teramoto, J. Nakayama, Sulfur Lett., 18, 237 (1995)
44. A. Ishii, Y.-N. Jin, M. Hoshino, J. Nakayama, Heteroatom Chem., 6, 161 (1995)
45. A. Ishii, M.-X. Ding, J. Nakayama, M. Hoshino, J. Chem. Soc., Chem. Commun., 1992, 7;
46. A. Ishii, M.-X. Ding, J. Nakayama, M. Hoshino. Bull. Chem. Soc. Jpn., 66, 1714 (1993)
47. A. Ishii, Y.-N. Jin. H. Nagaya, M. Hoshino, J. Nakayama, Tetrahedron Lett., 36, 1867 (1995)
48. A. Ishii, K. Umezawa, J. Nakayama, Tetrahedron Lett., 38, 1431 (1997)
49. J.L. Kice, G.B. Large, Tetrahedron Lett., 1965, 3537;
50. W.E. Savige, A. Fava, Chem. Commun., 1965, 417;
51. L. Sagramora, P. Koch, A. Garbesi, A. Fava, Chem. Commun., ibid., 1967, 985;
52. F.A. Davis, R.H. Jenkins, Jr., S.B. Awad, O.D. Stringer, W.H. Watson, J. Galloy, J. Am. Chem. Soc., 104, 5412 (1982);
53. C. Nemecek, E. Dunach, H.B. Kagan, Nouv. J. Chim., 10, 761 (1986);
54. G. Carrea, B. Redigolo, S. Riva, S. Colonna, N. Gaggero, E. Battistel, D. Bianchi, Tetrahedron-.Asymmetry, 3, 1063 (1992);
55. M. Mikofajczyk, J. Drabowicz, J. Chem. Soc., Chem. Commun., 1976, 220;
56. J. Drabowics, M. Mikołajczyk, Tetrahedron Lett., 26, 5703 (1985);
57. J. Drabowicz, M. Pacholczyk, Phosphorus and Sulfur, 29, 257 (1987);
58. M. Mikołajczyk, J. Drabowicz, J. Am. Chem. Soc., 100, 2510 (1978);
59. R. Bauer, W. Breu, H. Wagner, J. Chromatogr., 541, 464 (1991);
60. W. E. Savige, J. Eager, J.A. Maclaren, C.M. Roxburgh, Tetrahedron Lett., 1974, 3289;
61. M. Kishi, S. Ishihara, T. Komeno, Tetrahedron, 30, 2135 (1974)
62. D. Rogers, Acta Cryst., A37, 734 (1987)
63. P. Koch, E. Ciuffarin, A. Fava, J. Am. Chem. Soc., 92, 5971 (1970)