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For example, see: (a) Harvey, R. G. Polycyclic Aromatic Hydrocarbons; Wiley-VCH, 1997. (b) Clar, E. Polycyclic Hydrocarbons; Academic: New York, 1964.
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(a) Zhang, F.-J.; Cortez, C.; Harvey, R. G. J. Org. Chem. 2000, 65, 3952. (b) Harvey, R. G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press, 1991; Chapter 4. (c) Di Raddo, P.; Chan, T. J. Org. Chem. 1982, 47, 1427. (d) Lehr, R. E.; Yagi, H.; Thakker, D. R.; Levin, W.; Conney, A. H.; Jerina, D. M. Carcinog.-Comprv. 1978, 3, 231. (e) Thakker, D. R.; Yagi, H.; Lu, A. Y. H.; Levin, W.; Conney, A. H.; Jerina, D. M. Proc. Natl. Acad. Sci. USA 1976, 73, 3381.
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4
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0007366865
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For some recent references, see: (a) Sami, S. M.; Dorr, R. T.; Alberts, D. S.; Remers, W. A. J. Med. Chem. 1993, 36, 765. (b) Motohashi, N.; Gollapudi, S. R.; Emrani, J.; Bhattiprolu, K. R. Cancer Invest. 1991, 9, 305. (c) Denny, W. A.; Rewcastle, G. W.; Baguley, B. C. J. Med. Chem. 1990, 33, 814. (d) Palmer, B. D.; Rewcastle, G. W.; Atwell, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1988, 31, 707.
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5
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Becker, F. F.; Banik, B. K. Bioorg. Med. Chem. Lett. 1998, 8, 2877. For an example, see: Jorgensen, K.; Ipsen, J. H. Biochem. Biophys. Acta 1991, 1062, 227.
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For some recent examples, see: (a) Cherubim, P.; Deady, L. W.; Dorkos, M.; Quazi, N. H.; Baguley, B. C.; Denny, W. A. Anti-cancer Drug Design 1993, 8, 429. (b) Palmer, B. D.; Lee, H. H.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1992, 35, 258.
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7
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0007454174
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Banik, B. K.; Venkatraman, M. S.; Mukhopadhyay, C.; Becker, F. F. Tetrahedron Lett. 1998, 39, 7243. Also see: (a) Banik, B. K.; Ghatak, A.; Venkatraman, M. S.; Becker, F. F. Synth. Commun. 2000, 30, 2701. (b) Banik, B. K.; Ghatak, A.; Mukhopadhyay, C.; Becker, F. F. J. Chem. Res. (S) 2000, 108.
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0007419546
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Banik, B. K.; Mukhopadhyay, C; Venkatraman, M. S.; Becker, F. F. Tetrahedron Lett. 1998, 39, 7247. Also see: (a) Banik, B. K.; Zegrocka, O.; Banik, I.; Hackfeld, L.; Becker, F. F. Tetrahedron Lett. 1999, 40, 6731. (b) Ghatak, A.; Becker, F. F.; Banik, B. K. Tetrahedron Lett. 2000, 41, 3793. (c) Basu, M. K.; Becker, F. F.; Banik, B. K. Tetrahedron Lett. 2000, 41, 5603. (d) Banik, B. K.; Suhendra, M.; Banik, I.; Becker, F. F. Synth. Commun. 2000, in press.
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(a) Ranu, B. C.; Ghosh, K.; Jana, U. J. Org. Chem. 1996, 61, 9546. (b) Heaney, H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 2, p 753. (c) Olah, G. A. Friedel-Crafts and Related Reactions; Interscience: New York, 1964.
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(a) Abu-Shqara, E.; Yang, C. X.; Harvey, R. G. J. Org. Chem. 1992, 57, 3312. (b) Minabe, M.; Cho, B. P.; Harvey, R. V. J. Am. Chem. Soc. 1989, 111, 3809. (c) Yoshida, M.; Hishida, K.; Minabe, M.; Suzuki, K. J. Org. Chem. 1980, 45, 1783. (d) Yoshida, M.; Minabe, M.; Suzuki, K. J. Org. Chem. 1979, 44, 3029. (e) Yoshida, M.; Nagayama, S.; Minabe, M.; Suzuki, K. J. Org. Chem. 1979, 44, 1915.
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Dewar, M. J. S.; Dennington, II, R. D. J. Am. Chem. Soc. 1989, 111, 3804. Chem 3-D Pro version 4.0 was used to obtain the starting geometries by doing MM2 calculations. DEWAR-PI was used to calculate the energies of the Wheland Intermediates in kcal/mol for substitution at each position. DEWAR-PI was available from the Quantum Chemistry Program Exchange (QCPE). Dewar, M. J. S.; Ruiz, J. M. QCPE Bull. 1988, 8, No. 1, 50.
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The reactions were carried out under a well-ventilated hood. Some of the compounds described here are potential carcinogens.
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