A convenient synthesis of Benzo[c]naphtho[2,1-p]chrysene

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7198-7199

  Hagen, Stefan ^a   Scott, Lawrence T ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010242978     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961045e     Document Type: Article

References (24)

1. The name benzo[c]naphtho[2,1-p]chrysene is in accord with the nomenclature for PAH recommended by the IUPAC and applied by Chemical Abstracts. The more common name in the chemical literature for compound 1 is tribenzo[c,i,o]triphenylene.
2. (a) Faust, R.; Vollhardt, K. P. C. 7th International Symposium of Novel Aromatics, Victoria, B.C., Canada, 1992; Poster 61.
3. (b) Mehta, G.; Raghava Sharma, G. V.; Krishna Kumar, M. A.; Vedavyasa, T. V.; Jemmis, E. D. J. Chem. Soc., Perkin Trans. 1 1995, 2529.
4. (c) Erickson, M. S.; Milliken, J. Polycyclic Arom. Compd. 1996, 8, 1.
5. (d) The successful conversion of 1 to benz[5,6]-as-indaceno[3,2,1,8,7-mnopqr]-indeno[4,3,2,1-cdef]chrysene has been presented: Hagen, S.; Bratcher, M. S.; Scott, L. T.; Zimmermann, G. 210th ACS National Meeting, New Orleans, 1996; Organic Division poster 52.
6. Laarhoven, W. H.; van Broekhoven, J. A. M. Tetrahedron Lett. 1970, 1, 73.
7. (a) Juriew, J.; Skorochodowa, T.; Merkuschew, J.; Winter, W.; Meier, H. Angew. Chem. 1981, 93, 285; Angew. Chem., Int. Ed. Engl. 1981, 20, 269.
8. (a) Juriew, J.; Skorochodowa, T.; Merkuschew, J.; Winter, W.; Meier, H. Angew. Chem. 1981, 93, 285; Angew. Chem., Int. Ed. Engl. 1981, 20, 269.
9. (b) Winter, W.; Langjahr, U.; Meier, H.; Merkuschew, J.; Juriew, J. Chem. Ber. 1984, 117, 2452.
10. (c) Meier, H. Angew. Chem. 1992, 104, 1425; Angew. Chem., Int. Ed. Engl. 1992, 31, 1399.
11. (c) Meier, H. Angew. Chem. 1992, 104, 1425; Angew. Chem., Int. Ed. Engl. 1992, 31, 1399.
12. For prior synthesis of 3 see: (a) Orchin, M.; Reggel, L.; Friedel, R. A. J. Am. Chem. Soc. 1949, 71, 2743. (b) Burnham, J. W.; Melton, R. G.; Eisenbraun, E. J.; Keen, G. W.; Hamming, M. C. J. Org. Chem. 1973, 38, 2783. (c) Holba, A. G.; Premasager, V., Barot, R. C., Eisenbraun, E. J. Tetrahedron Lett. 1984, 26, 571.
13. For prior synthesis of 3 see: (a) Orchin, M.; Reggel, L.; Friedel, R. A. J. Am. Chem. Soc. 1949, 71, 2743. (b) Burnham, J. W.; Melton, R. G.; Eisenbraun, E. J.; Keen, G. W.; Hamming, M. C. J. Org. Chem. 1973, 38, 2783. (c) Holba, A. G.; Premasager, V., Barot, R. C., Eisenbraun, E. J. Tetrahedron Lett. 1984, 26, 571.
14. For prior synthesis of 3 see: (a) Orchin, M.; Reggel, L.; Friedel, R. A. J. Am. Chem. Soc. 1949, 71, 2743. (b) Burnham, J. W.; Melton, R. G.; Eisenbraun, E. J.; Keen, G. W.; Hamming, M. C. J. Org. Chem. 1973, 38, 2783. (c) Holba, A. G.; Premasager, V., Barot, R. C., Eisenbraun, E. J. Tetrahedron Lett. 1984, 26, 571.
15. Pyrko, A. N. Zh. Org. Khim. 1992, 28, 215.
16. 5b In the present case, however, their approach did not result in 1 but gave instead its constitutional isomer naphtho[2,1-s]picene and the PAH phenanthro[1,2,3,4-ghi]perylene. These findings are still under investigation and will be published elsewhere.
17. The calculated differences in the heats of formation of 6a and 6b are 0.019 kcal/mol (PM3) and 0.042 kcal/mol (AM1).
18. c = 120±2°C); δ given for fast exchange at 160°C; Δv given for slow exchange at 25°C.
19. (a) House, H. O.; Koepsell, D. G.; Campbell, W. J. J. Org. Chem. 1972, 37, 1003.
20. (b) Ibuki, E.; Ozasa, S.; Fujioka, Y.; Mizutani, H. Bull. Chem. Soc. Jpn. 1982, 55, 845.
21. Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769.
22. (a) Scholz, M.; Dietz, F.; Muehlstaedt, M. Z. Chem. 1967, 7, 329.
23. (b) Scholz, M.; Dietz, F.; Muehlstaedt, M. Tetrahedron Lett. 1967, 665.
24. (c) Laarhoven, W. H.; Cuppen, T. H. J. M.; Nivard, R. J. F. Recl. Trav. Chim. Pays-Bas 1968, 87, 687.