Efficient synthesis of 4,5,9,10-tetrahydropyrene: A useful synthetic intermediate for the synthesis of 2,7-disubstituted pyrenes

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6888-6890

  Connor, Daniel M ^a   Allen, Scott D ^a   Collard, David M ^a   Liotta, Charles L ^a   Schiraldi, David A ^b  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b KoSa   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON; PYRENE DERIVATIVE;

CARCINOGENESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; NOTE; SYNTHESIS;

EID: 0032886227     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990257j     Document Type: Note

References (50)

1. Harvey, R. G. Polycyclic Aromatic Compounds; Wiley-VCH: New York, 1997.
2. (b) Clar, E. Polycyclic Hydrocarbons; Academic Press: London, 1964.
3. Vollmann, H.; Becker, H.; Corell, M.; Streck, H. Liebigs Ann. Chem. 1937, 531, 1-125.
4. El-Baykoumy, K. Chem. Res. Toxicol. 1992, 5, 585-590.
5. (b) Rice, J. E.; Rivenson, A.; Braley, J.; LaVoie, E. J. J. Toxicol. Environ. Health 1987, 21, 525-532.
6. Minabe, M.; Nakada, K. Bull. Chem. Soc. Jpn. 1985, 58, 1962-1967.
7. Brocklehurst, P. J.; Hemingway, E. U.S. Patent 3,657,139, April 18, 1972.
8. Dewar, M. J. S.; Dennington, R. D. J. Am. Chem. Soc. 1989, 111, 3804-3808.
9. Yamato, T.; Miyazawa, A.; Tashiro, M. Chem. Ber. 1993, 126, 2505-2512.
10. (b) Rodenburg, L.; Brandsma, R.; Tintel, C.; Thuijl, J. van; Lugtenburg, J.; Cornelisse, J. Recl. Trav. Chim. Pays-Bas 1986, 105, 156-161.
11. (c) Yozo, M.; Yamano, E.; Miyazawa, A.; Tashiro, M. J. Chem. Soc., Perkin Trans. 2 1996, 3, 359-364.
12. Van der Braken-van Leersum, A. M.; Tintel, C.; Van't Zelfde, M.; Cornelisse, J.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1987, 106, 120-128.
13. Harvey, R. G., Konieczny, M.; Pataki, J. J. Org. Chem. 1983, 48, 2930-2932.
14. Lee, H.; Harvey, R. G. J. Org. Chem. 1986, 51, 2847-2848.
15. Klassen, S. E.; Daub, G. H.; VanderJagt, D. L. J. Org. Chem. 1983, 48, 4861-4366.
16. (b) Miller, D. W.; Herreno-Saenz, D.; Huang, K. H.; Heinze, T. M.; Fu, P. P. J. Org. Chem. 1992, 57, 3746-3748.
17. Kreyenschmidt, M.; Baumgarten, M.; Tyutyulkov, N.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1957-1959.
18. (b) Kreyenschmidt, M.; Uckert, F.; Müllen, K. Macromolecules 1995, 28, 4577-4582.
19. Flammang, R.; Martin, R. H. Bull Soc. Chim. Belg. 1971, 80, 433-438.
20. Yamato, T.; Ide, S.; Tokuhisa, K.; Tashiro, M. J. Org. Chem. 1992, 57, 271-275.
21. (b) Umemoto, T.; Satani, S.; Sakata, Y.; Misumi, S. Tetrahedron Lett. 1975, 36, 3159-3162.
22. Bolton, R. J. Chem. Soc. 1964, 4637-4640.
23. (b) Minabe, M.; Mochizuki, H.; Yoshida, M.; Toda, T. Bull. Chem. Soc. Jpn. 1989, 62, 68-72.
24. (c) Harvey, R. G.; Schmolka, S.; Cortez, C.; Lee, H. Synth. Commun. 1988, 18, 2207-2210.
25. Baker, W.; McOmie, J. F. W.; Norman, J. M. J. Chem. Soc. 1951, 1114-1121.
26. (b) Boekelheide, V.; Anderson, P. H.; Hylton, T. A. J. Am. Chem. Soc. 1974, 96, 1558-1563.
27. Chatterjee, N. N.; Bose, A.; Roy, H. B. J. Indian Chem. Soc. 1947, 24, 169-172.
28. Padwa, A.; Doubleday: C.; Mazzu, A. J. Org. Chem. 1977, 42, 3271-3279.
29. Hanson, P. E.; Blaabjerg, O.; Berg, A. Acta Chem. Scand. B 1978, 32, 720-726.
30. Fu, P. P.; Lee, H. M.; Harvey, R. G. J. Org. Chem. 1980, 45, 2797-2803.
31. Friedman, S.; Metlin, S.; Svedi, A.; Wender, I. J. Am. Chem. Soc. 1959, 24, 1287-1289.
32. (c) Korre, S. C.; Klein, M. T.; Quann, R. J. Ind. Eng. Chem. Res. 1995, 34, 101-117.
33. (d) Yalpani, M. Chem. Ber. 1990, 123, 983-987.
34. (e) Berg, A.; Lam, J.; Hansen, P. E. Acta Chem. Scand. B 1986, 40, 665-667.
35. (f) Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K.; Steele, W. V. J. Chem. Thermodyn. 1993, 25, 729-761.
36. (g) Yalpani, M.; Köster, R. Chem. Ber. 1990, 123, 719-724.
37. (h) Cameron, J. M. L.; Cook, J. W.; Graham, W. J. Chem. Soc. 1945, 286-288.
38. Eisenbraun, E. J.; Webb, T. E.; Burnham, J. W.; Harris, L. E. Org. Prep. Proced. Int. 1971, 3, 249-254.
39. Harvey, R. G.; Halonen, M. J. Chromatogr. 1966, 25, 294-302.
40. Harvey, R. G. Synthesis 1970, 4, 161-172.
41. Harvey, R. G.; Rabideau, P. W. Tetrahedron. Lett. 1970, 42, 3695-3698.
42. (b) Schnieders, C.; Müllen, K.; Huber, W. Tetrahedron 1984, 40, 1701-1711.
43. Harvey, R. G.; Arzadon, L.; Grant, J.; Urberg, K. J. Am. Chem. Soc. 1969, 91, 4535-4541.
44. Rodenburg, L.; Floor, M.; Lefeber, A.; Cornelisse, J.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1988, 107, 1-8.
45. Musa, A.; Sridharan, B.; Lee, H.; Mattern, D. L. J. Org. Chem. 1996, 61, 5481-5484.
46. Staab, H. A.; Kirrstetter, R. G. H. Liebigs Ann. Chem. 1979, 886-898.
47. Paioni, R.; Jenny, W. Helv. Chim. Acta 1970, 53, 141-155.
48. Johnson, W. S.; Gutsche, C. D.; Offenhauer, R. D. J. Org. Chem. 1946, 68, 1648-1650.
49. Staab, H. A.; Sauer, M. Liebigs Ann. Chem. 1984, 742-760.
50. Jones, J. R.; Liotta, C. L.; Collard, D. M.; Schiraldi, D. S. Macromolecules, in press.