The reaction of dimethyldioxirane with chrysene: Formation of a trioxide

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8671-8674

  Murray, Robert W ^a   Singh, Megh ^a   Rath, Nigam ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHRYSENE; CHRYSENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0030602207     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02006-0     Document Type: Article

References (26)

1. 1. Chemistry of Dioxiranes. 34. Part 33: Murray, R.W.; Singh, M.; Rath, N.P. J. Org. Chem., submitted.
2. 2. a.) Harvey, R.G. Polycyclic Aromatic Hydrocarbons and Carcinogenesis, ACS Monograph No. 283, American Chemical Society, Washington, D.C., 1985.
3. b.) Harvey, R.G. Acc. Chem. Res. 1981,14, 218-226.
4. c.) Miller, E.C. Cancer Res. 1978, 42, 1479-1496.
5. d.) Dipple, A.; Moschel, R. C.; Bigger, C.A. in Chemical Carcinogens, Searle, C.E., Ed., American Chemical Society, Washington, D.C., 1984, 41-163.
6. 3. a.) Weinstein, I.B.; Jeffrey, A.M.; Jenette, K.W.; Blotstein, J.H.; Harvey, R.G.,-Harris, C.; Autrup, H.; Kasai, H.; Nakanishi, K. Science 1976, 193, 592-595.
7. b.) Grover, P.L.; Sims, P. Biochem. J. 1968, 110, 159-160.
8. c.) Boyd, D.R.; Jerina, D.M. in Small Ring Heterocycles, Vol. 42, Part 3, John Wiley, New York, 1985, 197-281.
9. d.) Shirwaiker, G.S.; Bhatt, M.V. in Advances in Heterocyclic Chemistry, Vol. 37, Katritzky, A.R., Ed., Academic Press, New York, 1984, 68-165.
10. 4. For reviews of the formation of cyclic polyepoxides see: a.) Adam, W.; Balci, M. Tetrahedron 1980, 36, 833-858.
11. b.) Reference 3(c).
12. 5. Mohler, D.L.; Vollhardt, K.P.C.; Wolff, S. Angew. Chem. Int. Ed. Engl. 1995, 34, 563-565.
13. 6. Charles, H.C.; Baker, R.J.; Trefonas, L.M.; Griffin, G.W. J. Chem. Soc., Chem Commun. 1980, 1075-1076.
14. 7. Murray, R.W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847-2853.
15. 8. For reviews see: a.) Murray, R.W. Chem. Rev. 1989, 89, 1187-1201.
16. b.) Curci, R. In Advances in Oxygenated Processes; Baumstark, A.L., Ed.; JAI Publishers: Greenwich, CT, 1990; Vol. 2, Chapter 1, pp 1-59.
17. c.) Adam, W.; Hadjiarapoglou, L.P.; Curci, R.; Mello, R. In Organic Peroxides; Ando, W., Ed.; Wiley, New York, 1992; Chapter 4, pp 195-219.
18. d.) Adam, W.; Curci, R.; Edwards, J.O. Acc. Chem. Res, 1989, 22, 205-211.
19. e.) Curci, R.; Dinoi, A.; Rubino, M.F. Pure Appl. Chem. 1995, 67, 811-822.
20. 9. Jeyaraman, R.; Murray, R.W. J. Am. Chem. Soc. 1984, 106, 2462-2463.
21. 10. Agarwal, S.K.; Boyd, D.R.; Jennings, W.B.; McGuckin, R.M.; O'Kane, G.A. Tetrahedron Lett. 1989, 30, 123-126.
22. 3 : C, 78.25; H, 4.38. Found C, 77.57; H, 4.48.
23. 12. Harvey, R.G.; Goh, S.H.; Cortez, C. J. Am. Chem. Soc. 1975, 97, 3468-3479.
24. 13. Nashed, N. T.; Bax, A.; Loncharich, R.J.; Sayer, J.M.; Jerina, D.M. J. Am. Chem. Soc. 1993, 115, 1711-1722.
25. 14. The cis stereochemistry in 5 may be due to an attractive dipole interaction between the strong dipole in 1 and the dipole in the first oxide. Trioxide 3 may be accompanied by a strereoisomeric trioxide. The reaction mixture contains trace quantities of other materials which have not yet been identified.
26. 15. Glusker, J.P.; Carrell, H.L.; Zacharias, D.E. Cancer Biochem. Biophys. 1974, 1, 43-52.