Comparison of the Mechanisms of Solvolysis and Rearrangement of K-Region vs. Non-K-Region Arene Oxides of Phenanthrene. Comparative Solvolytic Rate Constants of K-Region and Non-K-Region Arene Oxides

Journal of the American Chemical Society

Volumn 98, Issue 10, 1976, Pages 2965-2973

  Bruice, Paula Yurkanis ^a   Bruice, Thomas C ^a   Dansette, Patrick M ^b   Selander, Hans G ^b   Yagi, Haruhiko ^b   Jerina, Donald M ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343950455     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00426a048     Document Type: Article

References (32)

1. J. W. Daly, D. M. Jerina, and B. Witkop, Experientia, 28, 1129 (1972)
2. D. M. Jerina and J. W. Daly, Science, 185, 573 (1974)
3. P. Sims and P. L. Grover, Adv. Cancer Res., 20, 165 (1974)
4. C. A. Coulson, Adv. Cancer Res., 1, 1 (1953)
5. A. Pullman and B. Pullman, Adv. Cancer Res., 3, 117 (1955)
6. W. C. Herndon, Trans. N.Y. Acad. Sci., 38, 200 (1974).
7. H. Yagi and D. M. Jerina, J. Am. Chem. Soc., 95, 243 (1973)
8. P. Dansette and D. M. Jerina, J. Am. Chem. Soc., 96, 1224 (1974)
9. J. Booth, E. Boyland, and E. E. Turner, J. Chem. Soc., 1188 (1950).
10. S. H. Goh and R. Harvey, J. Am. Chem. Soc., 95, 242 (1973)
11. R. Criegee, B. Marchand, and H. Wannowius, Justus Liebigs Ann. Chem., 550, 99 (1942)
12. A. S. Day and J. L. Neumeyer, J. Med. Chem., 17, 1095 (1974)
13. J. R. Malay and T. C. Bruice, Anal. Biochem., 34, 275 (1970).
14. G. J. Kasperek and T. C. Bruice, J. Am. Chem. Soc., 94, 198 (1972).
15. H. Yagi, D. M. Jerina, G. J. Kasperek, and T. C. Bruice, Proc. Natl. Acad. Sci. U.S.A., 69, 1985 (1972)
16. G. J. Kasperek, T. C. Bruice, H. Yagi, N. Kaubisch, and D. M. Jerina, J. Am. Chem. Soc., 94, 7876 (1972)
17. P. Y. Bruice, G. J. Kasperek, T. C. Bruice, H. Yagi, and D. M. Jerina, J. Am. Chem., Soc., 95, 1673 (1973)
18. G. J. Kasperek, T. C. Bruice, P. Y. Bruice, H. Yagi, and D. M. Jerina, J. Am. Chem., Soc., 95, 6041 (1973).
19. D. L. Whalen, J. Am. Chem. Soc., 95, 3432 (1973).
20. G. Guroff, J. W. Daly, D. M. Jerina, J. Renson, B. Witkop, and S. Udenfriend, Science, 157, 1524 (1967)
21. G. J. Kasperek, T. C. Bruice, H. Yagi, and D. M. Jerina, J. Chem. Soc., Chem. Commun., 784 (1972).
22. R. E. Barnett and W. P. Jencks, J. Am. Chem. Soc., 91, 2358 (1969).
23. D. M. Jerina, J. W. Daly, B. Witkop, P. Zaltzmann-Nirenberg, and S. Udenfriend, Biochemistry, 9, 147 (1970)
24. R. M. DeMarinis, C. N. Filer, S. M. Waraszkiewicz, and G. A. Berchtold, J. Am. Chem. Soc., 96, 1193 (1974)
25. D. M. Johnson and T. C. Bruice, J. Am. Chem. Soc., 97, 6901 (1975)
26. C. D. Ritchie and P. O. I. Virtanen, J. Am. Chem. Soc., 95, 1882 (1973).
27. A. Balsamo, G. Bertl, P. Crotti, M. Ferretti, B. Macchia, and F. Macchia, J. Org. Chem., 39, 2596 (1974).
28. C. Battistini, A. Balsamo, G. Berti, B. Crotti, B. Macchia, and F. Macchia, J. Chem. Soc., Chem. Commun., 712 (1974)
29. C. Battistini, P. Crotti, and P. Macchia, Tetrahedron Lett., 2091 (1975).
30. P. Y. Bruice, T. C. Bruice, H. G. Selander, H. Yagi, and D. M. Jerina, J. Am. Chem. Soc., 96, 6814 (1974)
31. D. R. Boyd, J. W. Daly, and D. M. Jerina, Biochemistry, 11, 1961 (1972).
32. D. M. Jerina, J. W. Daly, and B. Witkop, J. Am. Chem. Soc., 90, 6523 (1968)