A practical, large scale synthesis of the corannulene system [19]

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6323-6324

  Sygula, Andrzej ^a   Rabideau, Peter W ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; CORANNULENE; FULLERENE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL MODIFICATION; CHEMICAL REACTION; HYDROLYSIS; LETTER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034608923     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0011461     Document Type: Letter

References (34)

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18. 4 in THF gives corannulene and some dihydro- and tetrahydrocorannulenes. This mixture can be converted to pure corannulene with DDQ, but the yield of the two steps is only ca. 30%.
19. 5b
20. +) 634.2364, found 634.2375.
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22. See for example: (a) Hauser, C. R.; Brasen, W. R.; Skell, P. S.; Kantor, S. W.; Brodhag, A. E. J. Am. Chem. Soc. 1956, 78, 1653-1658. (b) Ledwith, A.; Shih-Lin, Y. Chem. Ind. (London) 1964, 1867-1868. (c) Hoeg, D. F.; Lusk, D. I. J. Organomet. Chem. 1966, 5, 1-12. (d) Hanna, S. B.; Wideman, L. G. Chem. Ind. (London) 1968, 486. (e) Vernigor, E. M.; Shalaev, V. K.; Luk'yanets, E. A. J. Org Chem. USSR 1981, 17, 317-321.
23. See for example: (a) Hauser, C. R.; Brasen, W. R.; Skell, P. S.; Kantor, S. W.; Brodhag, A. E. J. Am. Chem. Soc. 1956, 78, 1653-1658. (b) Ledwith, A.; Shih-Lin, Y. Chem. Ind. (London) 1964, 1867-1868. (c) Hoeg, D. F.; Lusk, D. I. J. Organomet. Chem. 1966, 5, 1-12. (d) Hanna, S. B.; Wideman, L. G. Chem. Ind. (London) 1968, 486. (e) Vernigor, E. M.; Shalaev, V. K.; Luk'yanets, E. A. J. Org Chem. USSR 1981, 17, 317-321.
24. See for example: (a) Hauser, C. R.; Brasen, W. R.; Skell, P. S.; Kantor, S. W.; Brodhag, A. E. J. Am. Chem. Soc. 1956, 78, 1653-1658. (b) Ledwith, A.; Shih-Lin, Y. Chem. Ind. (London) 1964, 1867-1868. (c) Hoeg, D. F.; Lusk, D. I. J. Organomet. Chem. 1966, 5, 1-12. (d) Hanna, S. B.; Wideman, L. G. Chem. Ind. (London) 1968, 486. (e) Vernigor, E. M.; Shalaev, V. K.; Luk'yanets, E. A. J. Org Chem. USSR 1981, 17, 317-321.
25. See for example: (a) Hauser, C. R.; Brasen, W. R.; Skell, P. S.; Kantor, S. W.; Brodhag, A. E. J. Am. Chem. Soc. 1956, 78, 1653-1658. (b) Ledwith, A.; Shih-Lin, Y. Chem. Ind. (London) 1964, 1867-1868. (c) Hoeg, D. F.; Lusk, D. I. J. Organomet. Chem. 1966, 5, 1-12. (d) Hanna, S. B.; Wideman, L. G. Chem. Ind. (London) 1968, 486. (e) Vernigor, E. M.; Shalaev, V. K.; Luk'yanets, E. A. J. Org Chem. USSR 1981, 17, 317-321.
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33. A non-pyrolytic synthesis of dibenzo[a,g]corannulene by palladium-catalyzed intramolecular aryl-aryl coupling of 7,10-di(2-bromophenyl)-fluoranthene has just been reported: (a) Scott, L. T.; Reisch, H. Abstracts; National Meeting of the American Chemical Society, San Francisco, CA, March 2000, ORGN-515. (b) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427-1430. We thank Professor Larry Scott for sharing the manuscript with us.
34. A non-pyrolytic synthesis of dibenzo[a,g]corannulene by palladium-catalyzed intramolecular aryl-aryl coupling of 7,10-di(2-bromophenyl)-fluoranthene has just been reported: (a) Scott, L. T.; Reisch, H. Abstracts; National Meeting of the American Chemical Society, San Francisco, CA, March 2000, ORGN-515. (b) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427-1430. We thank Professor Larry Scott for sharing the manuscript with us.