Polycyclic Arene Sulfides. Preparation of 1a,2,3,11b-Tetrahydrobenz-[5,6]anthra[1,2-b]thiirene, 6b,7a,8,9-Tetrahydrobenzo[10,11]-chryseno[1,2-b]thiirene, and 7,8,8a,9a-Tetrahydrobenzo-[10,11]chryseno[3,4-b]thiirene

Journal of Heterocyclic Chemistry

Volumn 33, Issue 1, 1996, Pages 53-55

  Shalom, Yosef ^a   Kogan, Vladimir ^a   Badriah, Yacoub ^a   Harvey, Ronald G ^b   Blum, Jochanan ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003148915     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330110     Document Type: Article

References (23)

1. For a leading review see e.g., R. G. Harvey, Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity, Cambridge University Press, Cambridge, UK, 1991 and references cited therein.
2. Y. Ittah, I. Shahak and J. Blum, J. Org. Chem., 43, 397 (1978).
3. H. Glatt, G. Ludewig, K. L. Platt, F. Waechter, I. Yona, S. Ben-Shoshan, P. Jerushalmy, I. Blum and F. Oesch, Cancer Res., 45, 2600 (1985).
4. J. Blum, Y. Shalom and R. G. Harvey, unpublished results.
5. E. Vogel, E. Schmidbauer and H.-J. Altenbach, Angew. Chem., Int. Ed. Engl., 13, 736 (1974).
6. S. Kagabu and H. Prinzbach, Angew. Chem., Int. Ed. Engl., 14, 252 (1975); Tetrahedron Letters, 29 (1975).
7. S. Kagabu and H. Prinzbach, Angew. Chem., Int. Ed. Engl., 14, 252 (1975); Tetrahedron Letters, 29 (1975).
8. See e.g. [a] R. C. Peterson, A. L. Hebert, G. W. Griffin, I. Sarkar, O. P. Strausz and J. Font, J. Heterocyclic Chem., 10, 879 (1973); [b] G. W. Griffin, K. Ishikawa and S. K. Satra, J. Heterocyclic Chem., 13, 1369 (1976); [c] A. M. Jeffery, H. J. C. Yeh, D. M. Jerina, R. M. DeMarinis, C. H. Forster, D. E. Piccolo and G. A. Berchtold, J. Am, Chem. Soc., 96, 4929 (1974).
9. See e.g. [a] R. C. Peterson, A. L. Hebert, G. W. Griffin, I. Sarkar, O. P. Strausz and J. Font, J. Heterocyclic Chem., 10, 879 (1973); [b] G. W. Griffin, K. Ishikawa and S. K. Satra, J. Heterocyclic Chem., 13, 1369 (1976); [c] A. M. Jeffery, H. J. C. Yeh, D. M. Jerina, R. M. DeMarinis, C. H. Forster, D. E. Piccolo and G. A. Berchtold, J. Am, Chem. Soc., 96, 4929 (1974).
10. See e.g. [a] R. C. Peterson, A. L. Hebert, G. W. Griffin, I. Sarkar, O. P. Strausz and J. Font, J. Heterocyclic Chem., 10, 879 (1973); [b] G. W. Griffin, K. Ishikawa and S. K. Satra, J. Heterocyclic Chem., 13, 1369 (1976); [c] A. M. Jeffery, H. J. C. Yeh, D. M. Jerina, R. M. DeMarinis, C. H. Forster, D. E. Piccolo and G. A. Berchtold, J. Am, Chem. Soc., 96, 4929 (1974).
11. For some leading reviews on the syntheses of thiiranes see e.g.: [a] D. C. Ditter, Comprehensive Heterocyclic Chemistry, Vol 7, A. R. Katritzky, C. W. Rees and W. Lwowski, eds, Pergamon Press, Oxford, UK, 1984, Chapter 5.06; [b] A. V. Fokin, M. A. Allakhverdiev and A. F. Kolomiets, Russ. Chem. Rev., 59, 705 (1990).
12. For some leading reviews on the syntheses of thiiranes see e.g.: [a] D. C. Ditter, Comprehensive Heterocyclic Chemistry, Vol 7, A. R. Katritzky, C. W. Rees and W. Lwowski, eds, Pergamon Press, Oxford, UK, 1984, Chapter 5.06; [b] A. V. Fokin, M. A. Allakhverdiev and A. F. Kolomiets, Russ. Chem. Rev., 59, 705 (1990).
13. L. Gatterman, Ber., 28, 2869 (1895).
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19. K. Sindelář, J. Holubek, M. Ryska, I. Koruna and M. Protiva, Collect. Czech. Chem. Commun., 51, 2848 (1986).
20. Many partially hydrogenated polycyclic hydrocarbons and epoxide were reported to be as active or even more active carcinogens than the derivatives of fully aromatic compounds. See e.g., H. Marquette, P. L. Grover and P. Sims, Cancer Res., 36, 2059 (1976).
21. P. P. Fu, C. Cortez, K. B. Sukumaran and R. G. Harvey, J. Org. Chem., 44, 4265 (1979).
22. T. Takido, Y. Kobayashi and K. Itabashi, Synthesis, 779 (1986).
23. I. F. Waterfall and P. Sims, Biochem. J., 128, 265 (1972).