Stable Ion Studies of the Chrysene Skeleton. Protonation of Chrysene, 6-Halochrysenes, 6-Aeetylchrysene, and 4H-Cyclopenta[def]chrysene: NMR Studies of Charge Distribution in Chrysenium Cations and AM1 Calculations

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 4023-4028

  Laali, Kenneth K ^a   Hollenstein, Sandro ^a   Harvey, Ronald G ^b   Hansen, Poul Erik ^c  

^a KENT STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CHICAGO   (United States)

^c ROSKILDE UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000024817     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9620730     Document Type: Article

References (36)

1. Harvey, R. G. In Polycyclic Hydrocarbons and Carcinogenesis; Harvey, R. G. Ed.; ACS Symposium Series 283; American Chemical Society: Washington, DC, 1985; Chapter 3.
2. Fu, P. P.; Harvey, R. G. J. Chem. Soc., Chem. Commun. 1978, 585.
3. Fu, P. P.; Harvey, R. G. J. Org. Chem. 1979, 44, 3778.
4. Hecht, S. S.; Loy, M.; Mazzarese, R.; Hoffmann, D. J. Med. Chem. 1978, 21, 38.
5. Hecht, S. S.; Mazzarese, R.; Amin, S.; LaVoie, E.; Hoffmann, D. in Polynuclear Aromatic Hydrocarbons; Jones, P. W., Leber, P., Eds.; Ann Arbor Science: Ann Arbor, MI, 1979; pp 733-752.
6. Lee-Ruff, E.; Kruk, H.; Katz, M. J. Org. Chem. 1984, 49, 553.
7. Harvey, R. G.; Pataki, J.; Cortez, C.; Di Raddo, P.; Yang, C. X. J. Org. Chem. 1991, 56, 1210. Yang, C. X.; Harvey, R. G. Tetrahedron 1992, 48, 3735.
8. Harvey, R. G.; Pataki, J.; Cortez, C.; Di Raddo, P.; Yang, C. X. J. Org. Chem. 1991, 56, 1210. Yang, C. X.; Harvey, R. G. Tetrahedron 1992, 48, 3735.
9. Dai, W. D.; Abu-Shqara, Harvey, R. G. J. Org. Chem. 1995, 60, 4905.
10. Lehr, R. E.; Kumar, S.; Levin, W.; Wood, A. W.; Chang, R. L.; Conney, A. H.; Yagi, H.; Sayer, J. M.; Jerina, D. M. In Polynuclear Aromatic Hydrocarbons and Carcinogenesis; Harvey, R. G., Ed.; ACS Symposium Series 283; American Chemical Society: Washington, DC, 1985; Chapter 4.
11. Wood, A. W.; Levin, W.; Chang, R. L.; Yagi, H.; Thakker, D. R.; Lehr, R. E.; Jerina, D. M.; Conney, A. H. In Polycyclic Aromatic Hydrocarbons; Jones, P. W., Leber, P. Eds.; Ann Arbor Science Publishers, Inc.: Ann Arbor, MI, 1979; pp 531-551.
12. Lowe, J. P.; Silverman, B. D. J. Am. Chem. Soc. 1984, 106, 5955. Lowe, J. P.; Silverman, B. D. J. Am. Chem. Soc. 1981, 1031 2852.
13. Lowe, J. P.; Silverman, B. D. J. Am. Chem. Soc. 1984, 106, 5955. Lowe, J. P.; Silverman, B. D. J. Am. Chem. Soc. 1981, 1031 2852.
14. Archer, W. J.; Taylor, R.; Gore, P. H.; Kamounah, F. S. J. Chem. Soc., Perkin. Trans. 2 1980, 1828.
15. Taylor, R. Electrophilic Aromatic Substitution; Wiley Interscience: Chichester, 1990; Chapter 3.
16. Reference 13, Chapter 6.
17. Review: Laali, K. K. Chem. Rev. 1996, 96, 1873.
18. Laali, K. K.; Hansen, P. E. Res. Chem. Intermed. 1996, 22, 737.
19. Laali, K. K.; Houser, J. J. J. Chem. Soc., Perkin. Trans. 2 1996, 1265.
20. Laali, K. K.; Hansen, P. E.; Laali, R. K.; Hansen, P. E.; Houser, J. J.; Zander, M. J. Chem. Soc., Perkin Trans. 2 1995, 1781.
21. Laali, K. K.; Hansen, P. E. J. Chem. Soc., Perkin Trans. 2 1995, 537
22. Laali, K. K.; Hansen, P. E. J. Chem. Soc., Perkin Trans. 2 1994, 2249 and references cited therein.
23. Abu-Shaqara, E.; Yang, C. X.; Harvey, R. G. J. Org. Chem. 1992, 57, 3312.
24. Hansen, P. E.; Berg, A.; Jakobson, H. J.; Manzara, A. P. Org. Magn. Reson. 1977, 10, 179.
25. Martin, R. H.; Morian, J.; Defay, N. Tetrahedron 1974, 30, 179.
26. 1H FT NMR Spectra; Aldrich Chemical Co.: Milwaukee, WI, 1993.
27. Laali, K. K.; Hollenstein, S.; Hansen, P. E. J. Org. Chem., submitted.
28. Bartle, K. D.; Smith, J. A. S. Spectrochim. Acta 1967, 23A, 1689.
29. Dewar, M. J. S.; Kelemen, J. J. Chem. Phys. 1968, 49, 499.
30. 13C is reasonable (see the supporting information); minor variations in the chemical shift of these carbons do not affect the deduced charge delocalization mode.
31. Laali, K. K.; Hansen, P. E. J. Org. Chem. 1993, 58, 4096.
32. Prakash Reddy, V.; Bellew, D. R.; Prakash, G. K. S. J. Fluorine Chem. 1992, 56, 195.
33. Reference 13, Chapter 9, and references cited therein.
34. Badger, G. M.; Stephens, J. F. J. Chem. Soc. 1956, 3637.
35. Gore, P. H.; Kamounah, F. S.; Miri, A. Y. J. Chem. Res., Synop. 1980, 40.
36. Laali, K. K.; Koser, G. F.; Subramanyam, S.; Forsyth, D. A. J. Org. Chem. 1993, 58, 1385.