Dibenz[a,c]anthracene: Electrophilic substitution and synthesis of phenol isomers

Tetrahedron

Volumn 53, Issue 47, 1997, Pages 15947-15956

  Harvey, Ronald G ^a   Aboshkara, Elias ^a   Pataki, John ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIBENZ[A,C]ANTHRACENE;

ARTICLE; BROMINATION; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; ISOMER; PRIORITY JOURNAL; STRUCTURE ANALYSIS; TOXIN ANALYSIS; TOXIN STRUCTURE;

EID: 0030707675     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10065-5     Document Type: Article

References (20)

1. Harvey, R. G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenesis, Cambridge University Press: Cambridge, England, 1991, pp. 191-193.
2. Slaga, T. J.; Gleason, G. L.; Mills, G.; Ewald, L.; Fu, P. P.; Lee, H. M.; Harvey, R. G. Cancer Res. 1980, 40, 1981.
3. Dewar, M. J. S. J. Am. Chem. Soc. 1952, 74, 3357.
4. Hites, R. A.; Simonsick, W. J., Jr. Calculated Molecular Properties of Polycyclic Aromatic Hydrocarbons, Elsevier: Amsterdam, 1987.
5. Harvey, R. G. Polycyclic Aromatic Hydrocarbons Wiley-VCH: New York, NY, 1997, pp. 140-144.
6. Iverson, B.; Sydnes, K. L.; Greibrokk, T. Acta Chem. Scand. 1985, B39, 837.
7. Bay region protons with an adjacent substituent generally appear as a singlet or a doublet with small meta coupling at relatively low field.
8. The technique of deuterium substitution coupled with NMR analysis to determine the site of bromine substitution was reported earlier: Minabe, M.; Cho, B.; Harvey, R. G. J. Am. Chem. Soc. 1989, 111, 3809.
9. (a) Kole, P. L.; Dubey, S. K.; Kumar, S. J. Org. Chem. 1989, 54, 845.
10. (b) Lee, H.; Harvey, R. G.; J. Org. Chem. 1983, 48, 749.
11. (c) Harvey, R. G.; Fu, P. P. J. Org. Chem. 1980, 45, 169.
12. Ashe III, A. J.; Kampf, J. W.; Savla, P. M. J. Org. Chem. 1990, 55, 5558.
13. Harvey, R. G.; Leyba, C.; Konieczny, M.; Fu, P. P.; Sukumaran, K. B. J. Org. Chem. 1978, 43, 3423.
14. Bhatt, M. V. Tetrahedron 1964, 20, 803. Schmidt, J.; Eitel, M. J. Prakt. Chem. 1932, 134, 167.
15. Bhatt, M. V. Tetrahedron 1964, 20, 803. Schmidt, J.; Eitel, M. J. Prakt. Chem. 1932, 134, 167.
16. Sukumaran, K. B.; Harvey, R. G. J. Org. Chem. 1980, 45, 4407.
17. (a) Harvey, R. G.; Cortez, C.; Jacobs, S. A. J. Org. Chem. 1982, 47, 2120.
18. (b) Beak, P.; Brown, R. A. J. Org. Chem. 1977, 42, 1823.
19. 2 provides equally satisfactory results.
20. Harvey, R. G.; Ray, K. J.; Sukumaran, K. B. Org. Prep. Proc. Internat. 1983, 15, 335.