Lowering inversion barriers of buckybowls by benzannelation of the rim: Synthesis and crystal and molecular structure of 1,2-dihydrocyclopenta[b,c]dibenzo[g,m]corannulene

Organic Letters

Volumn 3, Issue 22, 2001, Pages 3527-3529

  Marcinow, Zbigniew ^a   Sygula, Andrzej ^a   Ellern, Arkady ^a   Rabideau, Peter W ^a  

^a IOWA STATE UNIVERSITY   (United States)

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ARTICLE;

EID: 0001239671     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016607h     Document Type: Article

References (31)

1. For recent reviews, see: (a) Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-242.
2. (b) Scott, L. T. Pure Appl. Chem. 1996, 68, 291-300.
3. (c) Mehta, G.; Rao, H. S. P. Tetrahedron 1998, 54, 13325-13370.
4. (d) Scott, L. T.; Bronstein, H. E.; Preda, D. V.; Anselms, R. B. M.; Bratcher, M. S.; Hagen, S. Pure Appl. Chem. 1999, 71, 209-219.
5. (a) Seiders, T. J.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1996, 118, 2754-2755.
6. (b) Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1998, 120, 12666-12667.
7. (c) Seiders, T. J.; Baldrige, K. K.; Elliott, E. L.; Grube, G. H.; Siegel, J. S. J. Am. Chem. Soc. 1999, 121, 7439-7440.
8. (d) Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1999, 121, 7800-7803.
9. (e) Seiders, T. J.; Elliott, E. L.; Grube, G. H.; Siegel, J. S. J. Am. Chem. Soc. 1999, 121, 7804-7813.
10. (f) Reish, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427-1430.
11. (g) Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 2000, 122, 6323-6324.
12. (h) Sygula, A.; Marcinow, Z.; Fronczek, F. R.; Guzei, I.; Rabideau, P. W. Chem. Commun. 2000, 2439-2440.
13. (i) Seiders, T. J.; Baldridge, K. K.; Grube, G. H.; Siegel, J. S. J. Am. Chem. Soc. 2001, 123, 517-525.
14. Trost, B. M. J. Am. Chem. Soc. 1969, 91, 918-923.
15. 16 376.1252, found 376.1258.
16. -3; F(000) = 984; T= 173 K; R = 0.0385. Rw = 0.0868 for 5538 observed data. Intensity data were collected on a Bruker CCD-1000 diffractometer with Mo-Kα radiation (λ = 0.71073 Å). Hydrogen atoms were refined in isotropic approximation. See Supporting Information for crystallographic data in CIF format.
17. Sygula, A.; Folsom, H. E.; Sygula, R.; Abdourazak, A. H.; Marcinow, Z.; Fronczek, F. R.; Rabideau, P. W. Chem. Commun. 1994, 2571-2572.
18. Forkey, D. M.; Attar, S.; Noll, B. C.; Koerner, R.; Olmstead, M. M.; Balch, A. L. J. Am Chem. Soc. 1997, 119, 5766-5767.
19. Hanson, J. C.; Nordman, C. E. Acta Crystallogr. 1976, B32, 1147-1153.
20. Haddon, R. C.; Scott, L. T. Pure Appl. Chem. 1986, 58, 137. Haddon, R. C. Acc. Chem. Res. 1988, 21, 243. Haddon, R. C. J. Am. Chem. Soc. 1990, 112, 3385. Haddon, R. C. Science 1993, 261, 1543.
21. Haddon, R. C.; Scott, L. T. Pure Appl. Chem. 1986, 58, 137. Haddon, R. C. Acc. Chem. Res. 1988, 21, 243. Haddon, R. C. J. Am. Chem. Soc. 1990, 112, 3385. Haddon, R. C. Science 1993, 261, 1543.
22. Haddon, R. C.; Scott, L. T. Pure Appl. Chem. 1986, 58, 137. Haddon, R. C. Acc. Chem. Res. 1988, 21, 243. Haddon, R. C. J. Am. Chem. Soc. 1990, 112, 3385. Haddon, R. C. Science 1993, 261, 1543.
23. Haddon, R. C.; Scott, L. T. Pure Appl. Chem. 1986, 58, 137. Haddon, R. C. Acc. Chem. Res. 1988, 21, 243. Haddon, R. C. J. Am. Chem. Soc. 1990, 112, 3385. Haddon, R. C. Science 1993, 261, 1543.
24. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.: Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Goraperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
25. Sygula, A.; Abdourazak, A. H.; Rabideau, P. W. J. Am. Chem. Soc. 1996, 118, 339-343.
26. Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011.
27. Dynamic NMR simulations were done with the MEXICO method (Bain, A. D.; Duns. G. J. Can. J. Chem. 1996, 74, 819-824.) implemented into SpinWorks program package (SpinWorks, v.1.2; Kirk Marat and the University of Manitoba: Winnipeg, MB, Canada, copyright 2001; available from pauli.chem.umanitoba.ca.)
28. Dynamic NMR simulations were done with the MEXICO method (Bain, A. D.; Duns. G. J. Can. J. Chem. 1996, 74, 819-824.) implemented into SpinWorks program package (SpinWorks, v.1.2; Kirk Marat and the University of Manitoba: Winnipeg, MB, Canada, copyright 2001; available from pauli.chem.umanitoba.ca.)
29. According to a personal communication from L. T. Scott, the bowl-to-bowl inversion barrier for a dimethylcarbinol derivative of benzocorannulene is ca. 9.0 kcal/mol at -90 °C (McComas, C. C., B.S. Thesis. Boston College, 1996). and the barrier for a dimethylcarbinol derivative of dibenzo-[a,g]corannulene is <7.5 kcal/mol at -114 °C (Bratcher, M. S., Ph.D. Dissertation, Boston College, 1996). Both numbers are lower than the inversion barrier of dimethylcarbinol derivative of corannulene (10.2 kcal/ mol at -64 °C. Scott, L. T.; Hashemi, M. M.; Bratcher, M. S. J. Am. Chem. Soc. 1992, 114, 1920-1921).
30. According to a personal communication from L. T. Scott, the bowl-to-bowl inversion barrier for a dimethylcarbinol derivative of benzocorannulene is ca. 9.0 kcal/mol at -90 °C (McComas, C. C., B.S. Thesis. Boston College, 1996). and the barrier for a dimethylcarbinol derivative of dibenzo-[a,g]corannulene is <7.5 kcal/mol at -114 °C (Bratcher, M. S., Ph.D. Dissertation, Boston College, 1996). Both numbers are lower than the inversion barrier of dimethylcarbinol derivative of corannulene (10.2 kcal/ mol at -64 °C. Scott, L. T.; Hashemi, M. M.; Bratcher, M. S. J. Am. Chem. Soc. 1992, 114, 1920-1921).
31. According to a personal communication from L. T. Scott, the bowl-to-bowl inversion barrier for a dimethylcarbinol derivative of benzocorannulene is ca. 9.0 kcal/mol at -90 °C (McComas, C. C., B.S. Thesis. Boston College, 1996). and the barrier for a dimethylcarbinol derivative of dibenzo-[a,g]corannulene is <7.5 kcal/mol at -114 °C (Bratcher, M. S., Ph.D. Dissertation, Boston College, 1996). Both numbers are lower than the inversion barrier of dimethylcarbinol derivative of corannulene (10.2 kcal/ mol at -64 °C. Scott, L. T.; Hashemi, M. M.; Bratcher, M. S. J. Am. Chem. Soc. 1992, 114, 1920-1921).