Preparation of Condensed Aromatics by Superacidic Dehydrative Cyclization of Arvl Pinacols and Eooxides

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6666-6671

  Klumpp, Douglas A ^a   Baek, Donald N ^b   Prakash, G K Surya ^b   Olah, George A ^b  

^a CALIFORNIA STATE POLYTECHNIC UNIVERSITY   (United States)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001268744     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970293n     Document Type: Article

References (50)

1. (a) Chemistry in Superacids. 23. For part 22, see: Olah, G. A.; Rasul, G. J. Am. Chem. Soc. 1996, 118, 8503.
2. (b) Undergraduate research participant.
3. (a) Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 3, p 721.
4. (b) March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p 1072.
5. (c) Collins, C. J. Q. Rev. 1960, 14, 357.
6. (a) Bartok, M.; Molnar, A. In The Chemistry of Functional Groups; Patai, S., Ed.; Wiley: New York, 1980; Suppl. E; p 721.
7. (b) Bachmann, W. E. Organic Syntheses; Blatt, A. H., Ed.; Wiley: New York, 1943; Collect. Vol. 2, p 73.
8. (c) Pocker, Y.; Ronald, B. P. J. Org. Chem. 1970, 35, 3362.
9. (d) Gebhart, H. J., Jr.; Adams, K. H. J. Am. Chem Soc. 1954, 76 , 3925.
10. (e) Hill, G. A.; Flosdorf, E. W. Organic Syntheses, Gilman, H., Ed.; Wiley: New York, 1941; Collect. Vol. 1, 2nd ed.; p 462.
11. (f) Pocket, Y.; Ronald, B. P. J. Am. Chem Soc. 1970, 92, 3385.
12. Olah, G. A.; Klumpp, D. A.; Never, G.; Wang, Q. Synthesis 1996, 321. For a review of triflic acid chemistry, see: Stang, P. J.; White, M. R. Aldrichimica Acta 1983, 16, 15.
13. Olah, G. A.; Klumpp, D. A.; Never, G.; Wang, Q. Synthesis 1996, 321. For a review of triflic acid chemistry, see: Stang, P. J.; White, M. R. Aldrichimica Acta 1983, 16, 15.
14. Olah, G. A.; Klumpp, D. A. Abstract of Papers, 211st National Meeting of the American Chemical Society, Chicago, IL, August 1995; American Chemical Society: Washington, DC, 1995; Abstract ORGN 17.
15. (a) Saito, S.; Saito, S.-i.; Ohwada, T.; Shudo, K. Chem. Pharm. Bull. 1991, 39, 2718.
16. (b) For a general discussion of superacids, see: Olah, G. A.; Prakash, G. K. S.; Sommer, J. Superacids; Wiley: New York, 1985.
17. (a) Saito, S.; Sato, Y.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1994, 116, 2312.
18. (b) Shudo, K.; Ohwada, T. In Stable Carbocation Chemistry; Prakash, G. K. S., Schleyer, P. v. R., Eds.; Wiley: New York, 1997; pp 540-541.
19. (a) Olah, G. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 767.
20. (b) Ohwada, T.; Yagamata, N.; Shudo, K. J. Am. Chem. Soc. 1991, 113, 1364.
21. (c) Yamazaki, T.; Saito, S.-i.; Ohwada, T.; Shudo, K. Tetrahedron Lett. 1995, 36, 5749.
22. (d) Olah, G. A.; Ramaiah, P.; Wang, Q.; Prakash, G. K. S. J. Org. Chem. 1993, 58, 6900.
23. (e) Hartz, N.; Rasul, G.; Olah, G. A. J. Am. Chem. Soc. 1993, 155, 1277.
24. (f) Olah, G. A.; Rasul, G.; Aniszfeld, R.; Prakash, G. K. S. J. Am Chem. Soc. 1992, 114, 5608.
25. (g) Berkessel, A.; Thauer, R. K. Angew. Chem., Int. Ed. Engl. 1995, 34, 2247.
26. (a) Olah, G. A.; Grant, J. L.; Spear, R. J.; Bollinger, J. M.; Serianz, A.; Sipor, G. J. Am. Chem. Soc. 1976, 98 , 2501.
27. (b) As suggested by a referee, the cyclization of 7 may be thought of as an electrocyclization reaction followed by the loss of two protons. This cyclization mecha nism may also explain the observed regioselectivity in the formation of products 3f-j. A dication such as 7 would tend to delocalize positive charge into the more electron rich rings, which would then cyclize and lead to products 3f-j.
28. (a) Schmidlin, J.; Escher, R. Chem. Ber. 1910, 43, 1153.
29. (b) Schoepfle, C. S.; Ryan, J. D. J. Am. Chem. Soc. 1932, 54, 3687.
30. (a) Gore, P. H. In Freidel-Crafts and Related Reactions; Olah. G. A., Ed.; Interscience: New York, 1964; Vol. 3, Chapter 31.
31. (b) Taylor, R. Electrophilic Aromatic Substitution; Wiley: New York, 1990; Chapter 2.
32. 3; R = 0.07.
33. Mitchell, R. H.; Fyles, T.; Ralph, L. M. Can. J. Chem. 1977, 55, 1480.
34. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon; New York, 1988.
35. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
36. (a) Schonburg, A.; Mustafa, A. Chem. Rev. 1947, 40, 181.
37. (b) Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; CRC Press: Boca Raton, FL, 1991; p 302.
38. Zeigler, H. E.; Wo, S. J. Org. Chem. 1995, 60, 5925.
39. Analytical data found in ref 4.
40. Sato, R.; Nagaoka, T.; Saito, M. Tetrahedron Lett. 1990, 31, 5749.
41. Products 3f and 3g exhibited complex NMR spectra at ambient temperature, suggesting that the aryl rings in the 9,10 positions of the phenanthrenes possess restricted rotation.
42. Hatt, H. H. J. Chem. Soc. 1929, 1623.
43. (a) Acree, S. F. J. Am. Chem. Soc. 1912, 34, 3687.
44. (b) Moriconi, E. J.; O'Connor, W. F.; Kuhn, L. P.; Keneally, E. A.; Wallenberger, F. T. J. Am. Chem. Soc. 1959, 81, 6472.
45. Buchta, E.; Maar, H. Chem. Ber. 1962, 95, 1826.
46. 13C signals could not be observed.
47. (a) Trost, B. M. J. Am. Chem. Soc. 1966, 88, 853.
48. (b) Tatsugi, J.; Okumura, S.; Izawa, Y. Bull. Chem. Soc. Jpn. 1986, 59, 3311.
49. Gomberg, M.; Bachmann, W. E. J. Am. Chem. Soc. 1927, 49, 236.
50. Dias, J. R. Handbook of Polycyclic Hydrocarbons; Elsevier: New York, 1987.