Reactions of Benzyne with 1,3-Benzodithiole-2-thione and Related Compounds: Formation of Novel Tetracyclic Sulfonium Salts and Their Reactions Leading to Dibenzo-1,3,6,-trithiocin Derivatives

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 8, 1996, Pages 2349-2354

  Nakayama, Juzo ^a   Kimata, Atsuko ^a   Taniguchi, Hideki ^a   Takahashi, Fumihiko ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001632898     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.2349     Document Type: Article

References (35)

1. D. B. J. Easton and D. Leaver, J. Chem. Soc., Chem. Commun., 1965, 585; D. B. J. Easton, D. Leaver, and T. J. Rawlings, J. Chem. Soc., Perkin Trans, 1, 1972, 41.
2. D. B. J. Easton and D. Leaver, J. Chem. Soc., Chem. Commun., 1965, 585; D. B. J. Easton, D. Leaver, and T. J. Rawlings, J. Chem. Soc., Perkin Trans, 1, 1972, 41.
3. M. V. Lakshmikantham and M. P. Cava, J. Org. Chem., 41, 879 (1976).
4. a) H. Behringer and R. Wiedenmann, Tetrahedron Lett., 1965, 3705
5. b) H. Behringer and D. Deichmann, Tetrahedron Lett., 1967, 1013
6. c) H. Behringer, J. Kilger, and R. Wiedenmann, Tetrahedron Lett., 1968, 1185
7. d) H. Behringer, D. Bender, J. Falkenberg, and R. Wiedenmann, Chem. Ber., 101, 1428 (1968)
8. e) H. Davy. M. Demuynck, D. Paquer, A. Rouessac, and J. Vialle, Bull. Soc. Chim. Fr., 1966, 1150
9. f) D. Noel and J. Vialle, Bull. Soc. Chim. Fr., 1967, 2239
10. g) C. Gueden and J. Vialle, Bull. Soc. Chim. Fr., 1973, 270
11. h) R. Mayer, H. J. Hartmann, and J. Jentzsch, J. Prakt. Chem., 31, 312 (1966)
12. i) B. R. O'Connor and F. N. Jones, J. Org. Chem., 35, 2002 (1970)
13. j) J. E. Oliver and R. T. Brown, J. Org. Chem., 39, 2228 (1974)
14. k) J. Goerdeler, R. Büchler, and S. Sólyom, Chem. Ber., 110, 285 (1977)
15. l) K. Akiba, M. Ochiumi, T. Tsuchiya, and N. Inamoto, Tetrahedron Lett., 1975, 459
16. m) M. V. Lakshmikantham and M. P. Cava, J. Org. Chem., 41, 882 (1976).
17. B. H. Klanderman and T. R. Criswell, J. Org. Chem., 34, 3426 (1969).
18. For a preliminary report, see: J. Nakayama, A. Kimata, H. Taniguchi, and F. Takahashi, J. Chem. Soc., Chem. Commun., 1996, 205.
19. G. H. Senkler, Jr., B. E. Maryanoff, J. Stackhouse, J. D. Andose, and K. Mislow, in "Organic Sulphur Chemistry," ed by C. J. M. Stirling, Butterworths, London (1975), pp. 157-179.
20. V. Franzen, H. -I. Joschek, and C. Mertz, Justus Liebigs Ann. Chem., 654, 82 (1962).
21. J. Nakayama, K. Hoshino, and M. Hoshino, Chem. Lett., 1985, 677.
22. F. M. Logullo, A. H. Seitz, and L. Friedman, Org. Synth., Coll. Vol. 5, 54 (1973).
23. S. Asperger, D. Stefanovic, D. Hegedic, D. Pavlovic, and L. Klasinc, J. Org. Chem., 33, 2526 (1968).
24. Hydride abstraction of 1,3-dithioles by triphenylcarbenium salts affords the corresponding 1,3-dithiolium salts which are believed to be aromatic: A. Takamizawa and K. Hirai, Chem. Pharm. Bull., 17, 1931 (1969); K. Hirai, Tetrahedron, 27, 4003 (1971); J. Nakayama, K. Fujiwara, and M. Hoshino, Chem. Lett., 1975, 1099; I. Degani and R. Fochi, Synthesis, 1976, 759; I. Degani and R. Fochi, J. Chem. Soc., Perkin Trans. 1, 1976, 1886.
25. Hydride abstraction of 1,3-dithioles by triphenylcarbenium salts affords the corresponding 1,3-dithiolium salts which are believed to be aromatic: A. Takamizawa and K. Hirai, Chem. Pharm. Bull., 17, 1931 (1969); K. Hirai, Tetrahedron, 27, 4003 (1971); J. Nakayama, K. Fujiwara, and M. Hoshino, Chem. Lett., 1975, 1099; I. Degani and R. Fochi, Synthesis, 1976, 759; I. Degani and R. Fochi, J. Chem. Soc., Perkin Trans. 1, 1976, 1886.
26. Hydride abstraction of 1,3-dithioles by triphenylcarbenium salts affords the corresponding 1,3-dithiolium salts which are believed to be aromatic: A. Takamizawa and K. Hirai, Chem. Pharm. Bull., 17, 1931 (1969); K. Hirai, Tetrahedron, 27, 4003 (1971); J. Nakayama, K. Fujiwara, and M. Hoshino, Chem. Lett., 1975, 1099; I. Degani and R. Fochi, Synthesis, 1976, 759; I. Degani and R. Fochi, J. Chem. Soc., Perkin Trans. 1, 1976, 1886.
27. Hydride abstraction of 1,3-dithioles by triphenylcarbenium salts affords the corresponding 1,3-dithiolium salts which are believed to be aromatic: A. Takamizawa and K. Hirai, Chem. Pharm. Bull., 17, 1931 (1969); K. Hirai, Tetrahedron, 27, 4003 (1971); J. Nakayama, K. Fujiwara, and M. Hoshino, Chem. Lett., 1975, 1099; I. Degani and R. Fochi, Synthesis, 1976, 759; I. Degani and R. Fochi, J. Chem. Soc., Perkin Trans. 1, 1976, 1886.
28. Hydride abstraction of 1,3-dithioles by triphenylcarbenium salts affords the corresponding 1,3-dithiolium salts which are believed to be aromatic: A. Takamizawa and K. Hirai, Chem. Pharm. Bull., 17, 1931 (1969); K. Hirai, Tetrahedron, 27, 4003 (1971); J. Nakayama, K. Fujiwara, and M. Hoshino, Chem. Lett., 1975, 1099; I. Degani and R. Fochi, Synthesis, 1976, 759; I. Degani and R. Fochi, J. Chem. Soc., Perkin Trans. 1, 1976, 1886.
29. For this type of hydrolysis, for example, see: J. Meinwald, S. Knapp, S. K. Obendorf, and R. E. Hughes, J. Am. Chem. Soc., 98, 6643 (1976).
30. J. Drabowicz and M. Mikolajczyk, Synthesis, 1978, 138.
31. J. Nakayama, H. Sugiura, and M. Hoshino, Tetrahedron Lett., 24, 2585 (1983).
32. W. R. H. Hurtley and S. Smiles, J. Chem. Soc., 1926, 1821.
33. S. Hünig, G. Kiesslich, K. H. Oette, and H. Quast, Justus Liebigs Ann. Chem., 754, 46 (1971); E. Campaigne, T. Bosin, and R. D. Hamilton, J. Org. Chem., 30, 1677 (1965).
34. S. Hünig, G. Kiesslich, K. H. Oette, and H. Quast, Justus Liebigs Ann. Chem., 754, 46 (1971); E. Campaigne, T. Bosin, and R. D. Hamilton, J. Org. Chem., 30, 1677 (1965).
35. D. Greenwood and H. A. Stevenson, J. Chem. Soc., 1953, 1514.