The first synthesis and characterization of bisbenzotrithiole containing two benzotrithioles linked by an alkanedioxy spacer

Heterocycles

Volumn 55, Issue 5, 2001, Pages 851-854

  Sato, Ryu ^a   Utsumi, Yoshiyuki ^a   Nakajo, Shiduko ^a   Ogawa, Satoshi ^a   Kawai, Yasushi ^b  

^a IWATE UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

7,7' DIETHYL 4,4' ETHYLENEDIOXYBIS(BENZO[1,2 D][1,2,3]TRITHIOLE); BISBENZOTRITHIOLE; CHALCOGEN; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; ELECTROCHEMICAL ANALYSIS; OXIDATION REDUCTION REACTION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0035336036     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-01-9185     Document Type: Article

References (26)

1. a) F. Fehér and M. Langer, Tetrahedron Lett., 1971, 2125;
2. b) B. L. Chenard and T. J. Miller, J. Org. Chem., 1984, 49, 1221;
3. c) B. L. Chenard, R. L. Harlow, A. L. Johnson, and S. A. Vladuchick, J. Am. Chem. Soc., 1985, 107, 3871;
4. d) J. Nakayama, M. Kashiwagi, R. Yomoda, and Hoshino, Nippon Kagaku Kaishi, 1987, 1424.
5. F. D. Toste and W. J. Still, J. Am. Chem. Soc., 1995, 117, 7261.
6. a) K. Rasheed and J. D. Warkentin, J. Org. Chem., 1980, 45, 4806;
7. b) M. J. Plater and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1991, 317.
8. a) B. S. Davidson, T. F. Molinski, L. R. Barrows, and C. M. Ireland, J. Am. Chem. Soc., 1991, 113, 4709;
9. b) M. Litaudon and M. Guyot, Tetrahedron Lett., 1991, 32, 911;
10. c) V. Behar and S. J. Danishefsky, J. Am. Chem. Soc., 1993, 115, 7018;
11. d) P. W. Ford and B. S. Davidson, J. Org. Chem., 1993, 58, 4522;
12. e) P. W. Ford, M. R. Narbut, J. Belli, and B. S. Davidson, J. Org. Chem., 1994, 59, 5955.
13. a) R. Sato, S. Saito, H. Chiba, T. Goto, and M. Saito, Chem. Lett., 1986, 349;
14. b) R. Sato, S. Saito, H Chiba, T. Goto, and M. Saito, Bull. Chem. Soc. Jpn., 1988, 61, 1647;
15. c) R. Sato, T. Kimura, T. Goto, and M. Saito, Tetrahedron Lett., 1988, 29, 6291;
16. d) R. Sato, T. Kimura, T. Goto, M. Saito, and C. Kabuto, Tetrahedron Lett., 1989, 30, 3453.
17. a) S. Ogawa, N. Yomoji, S. Chida, and R. Sato, Chem. Lett., 1994, 507;
18. b) S. Ogawa, T. Kikuchi, A. Sasaki, S. Chida, and R. Sato, Tetrahedron Lett., 1994, 35, 5469.
19. R. Sato, T. Ohyama, T. Kawagoe, M. Baba, S. Nakajo, T. Kimura, and S. Ogawa, Heterocycles, 2001, 55, 145.
20. 6: C, 47.13; H, 3.96. Found: C, 47.00; H, 4.03.
21. max = 136.3°, R = 0.068, Rw = 0.093.
22. S. Ogawa, S. Saito, T. Kikuchi, Y. Kawai, S. Niizuma, and R. Sato, Chem. Lett., 1995, 321.
23. -1.
24. 3: C, 46.92; H, 4.38. Found: C, 46.95; H, 4.37.
25. 6: C, 28.88; H, 2.42. Found: C, 29.00; H, 2.52.
26. 2+* in MeCN as a solvent at 16 °C gave a value of g = 2.017 G.