Tetrahydronaphthalene derivatives by amberlyst® 15-promoted friedel-crafts cyclizations

Organic Preparations and Procedures International

Volumn 42, Issue 1, 2010, Pages 83-93

  Bunce, Richard A ^a   Cox, Andrew N ^a,b  

^a OKLAHOMA STATE UNIVERSITY   (United States)

^b Louisiana Tech University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMBERLYST-15; FRIEDEL-CRAFTS CYCLIZATION; TETRAHYDRONAPHTHALENES;

EID: 77950272854     PISSN: 00304948     EISSN: None     Source Type: Journal    
DOI: 10.1080/00304940903523553     Document Type: Article

References (35)

1. J. Vasudevan, A. T. Johnson, D. Huang, L. Wang and R. A. Roshantha, World Patent WO 2002018361 (2002);
2. Chem Abstt, 136, 216646 (2002).
3. G. Benoit, H. Gronemeyer, L. Hinrich, G. Michel and M. Gottardis, US Patent 6624154 (2003);
4. Chem. Abstt, 139, 255334 (2003).
5. M. Phahl, C. Tachdjian, H. A. Al-Shamma, A. Hussien, A. Fanjul, D. P. M. Pleynet, L. W. Spruce, R. Fine and J. W. Zapf, World Patent WO 2002072543 (2002);
6. Chem Abstr., 137, 226654 (2002).
7. Amberlyst® 15 Synthetic Resin Catalyst, Technical Bulletin - Fluid Process Chemicals, Rohm and Haas Company, Inc., Philadelphia, PA, 1978.
8. M. T. Bogert, D. Davidson and P. M. Apfelbaum, J. Am. Chem. Soc., 56, 959 (1934).
9. R. B. Miller and C. G. Gutierrez, J. Org. Chem., 43,1569 (1978).
10. Acids 1 and 3 are commercially available. Acid 2 was prepared from 4-chlorobenzoylpropanoic acid using the method developed by E. L. Martin, J. Am. Chem. Soc, 58, 1438 (1936) and
11. described in L. F. Fieser and M. Fieser. Reagents for Organic Synthesis, 1, 1287 ( 1967).
12. H. R. Harrison, W. M. Hay nes, P. Arthur and E. J. Eisenbraun, Chem. Ind. (London), 1568 (1968).
13. R. de Haan, E. W. de Zwart and J. Cornelisse, J. Pholochem. Photobiol A: Chem., 102, 179 (1997).
14. Benzene was generally used as the solvent for this study, but heptane also gave excellent results, see R. A. Bunce and H. D. Reeves, J. Chem Educ., 67, 69 (1990). It is likely that any unreactive hydrocarbon with a bp > 80°C can be used for this reaction.
15. Since alkenes 16b-18b could not be isolated in pure form, and longer reaction times (8 h) cleanly converted them to 1,1-diphenyl-1,2,3,4- tetrahydronaphthalenes 12b-14b, they were not fully characterized.
16. C. M. Clark and J. D. A. Johnson J. Chem. Soc., 126 (1962).
17. S. M. Smith, N. C. Thacker and J. M. Takacs, J. Am. Chem. Soc., 130, 3734 (2008).
18. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 43, 2923 (1978).
19. S. Inaba, H. Matsumoto and R. D. Rieke, J. Org. Chem., 49, 2093 (1984). Some spectral data have been published for this compound, but it is incomplete.
20. This compound has been previously reported, but detailed spectral data were not given, see M. Sugimori, A. Ejima, S. Ohsuki, K. Uoto, K. Mitsui, Y. Kawato, Y. Hirota, K. Sato and H. Terasawa, J. Med. Chem., 41, 2308 (1998).
21. M. Gates, D. L. Frank and W. C. von Feiten, J. Am. Chem. Soc, 96, 5138 (1974).
22. P. J. Kropp, G. W. Breton, S. L. Craig, S. D. Crawford, W. F. Durland, Jr., J. E. Jones, III, J. S. Raleigh, J. Org. Chem., 60, 4146 (1995).
23. This compound has been previously reported, but detailed spectral data were not given, seeref 6.
24. T. W. Campbell and W. G. Young, J. Am. Chem. Soc., 69, 3066 (1947).
25. This compound has been previously reported, but detailed spectral data were not given. Partial spectral data were reported in ref 6 and in W. L. Meyer, M. J. Brannon, C. G. Burgos, T. E. Goodwin and R. W. Howard, J. Org. Chem., 50, 438 (1985).
26. This compound has been previously reported but no spectral data were available, see E. A. Braude, L. M. Jackman, R. P. Linstead and G. Lowe, J. Chem. Soc, 3123 (1960).
27. A more recent paper had matching spectral data, but the reported mp was only 93-95°C, see B-Y. Wang, R-S. Jiang, J. Li and M. Shi, Eur. J. Org. Chem., 4002 (2005).
28. C. M. Rao Volla, S. R. Dubbaka and P. Vogel, Tetrahedron, 65, 504 (2009).
29. This compound has been previously reported, but no procedure or spectral data were given, see A. Franke, G. Mattem and W. Traber, Helv. Chim. Acta, 58, 293 (1975).
30. J. Balsevich, Can. J. Chem., 61, 1053 (1983).
31. This compound has been previously reported, but no procedure or spectral data were given, see J. W. Wilt and W. W. Pawlikowski, Jr., J. Org. Chem., 40, 3641 (1975)
32. and M. Clackers, D. M. Coe, D. A. Demaine, G. W. Hardy, D. Humphreys, G. G. A. Inglis, M. J. Johnston, et al., Bioorg. Med. Chem. Lett., 17, 4737 (2007).
33. This compound was prepared as generally described in A. Maercker, Org. React., 14,270 (1965)
34. and L. F. Fieser and M. Fieser, Reagents for Organic Synthesis, 1, 112 (1967).
35. W. S. Johnson and H. J. Glenn, J. Am. Chem. Soc, 71, 1087 (1949).