Synthesis and quantum mechanical structure of sym-pentamethylcorannulene and decamethylcorannulene [18]

Journal of the American Chemical Society

Volumn 121, Issue 32, 1999, Pages 7439-7440

  Seiders, T Jon ^a   Baldridge, Kim K ^a   Elliott, Eric L ^a   Grube, Gunther H ^a   Siegel, Jay S ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; CORANNULENE; NICKEL CHLORIDE; PALLADIUM; REAGENT; TITANIUM; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; QUANTUM MECHANICS; REACTION ANALYSIS; SOLUBILITY; SYNTHESIS;

EID: 0033581209     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991486q     Document Type: Letter

References (32)

1. Baldridge, K. K.; Siegel, J. S. Theor. Chem. Acta 1997, 97, 67-71.
2. (a) Seiders, T. J.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1996, 118, 2754-2755.
3. (b) Scott, L. T.; Cheng, P. C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963-10968.
4. (c) Zimmermann, G.; Nuechter, U.; Hagen, S.; Nuechter, M. Tetrahedron Lett. 1994, 35, 4747-4750.
5. (d) Mehta, G.; Panda, G. Tetrahedron Lett. 1997, 38, 2145-2148.
6. (e) Liu, C. Z.; Rabideau, P. W. Tetrahedron Lett. 1996, 37, 3437-3440.
7. Cheng, P.-C. Ph.D. Dissertation, Boston College, Boston, MA, 1996.
8. Scott, L. T. Pure Appl. Chem 1996, 68, 291-300.
9. Huang, R.; Huang, W.; Wang, Y.; Tang, Z.; Zheng, L. J. Am. Chem. Soc. 1997, 119, 5954-5955.
10. Farina, V. Comprehensive Organometallic Chemistry II: a Review of the Literature 1982-1994; Abel, E. W., Stone, F. G., Wilkinson, G., Eds.; Pergamon: Oxford, New York, 1995; Vol. 12, p 161.
11. Ayalon, A.; Sygula, A.; Cheng, P. C.; Rabinovitz, M.; Rabideau, P. W.; Scott, L. T. Science 1994, 265, 1065-1067.
12. Baumgarten, M.; Gherghel, L.; Wagner, M.; Weitz, A.; Rabinovitz, M.; Cheng, P. C.; Scott, L. T. J. Am. Chem. Soc. 1995, 117, 6254-6257.
13. 12) 264.0939, found 264.0926.
14. 20) 320.1565, found 320.1560.
15. 30) 390.2348, found 390.2347.
16. One might speculate that a coordinative interaction between TMA and the oxygen of DMEU heightens the reactivity of TMA in the mixture.
17. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Jensen, J. H.; Koseki, S.; Gordon, M. S.; Nguyen, K. A.; Windus, T. L.; Albert, S. T. QCPE Bull. 1990, 10.
18. Frisch, M. J., Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. J.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.6; Gaussian Inc.: Pittsburgh, PA, 1998.
19. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
20. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
21. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
22. Dunning, T. H. J. Chem. Phys. 1989, 90, 1007.
23. Martin, J. M. L. Chem. Phys. Lett. 1996, 262, 97-104.
24. Bowl depth is defined as the distance from the best plane of hub carbons to the best plane of the rim carbons.
25. Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-622.
26. For related work, see: Biedermann, P. B.; Pogodin, S.; Agranat, I. J. Org. Chem. 1999, 64, 3655-3662.
27. Qiao, X. X.; Ho, D. M.; Pascal, R. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1531-1532.
28. Seiders, T. J.; Elliott, E. L.; Grube, G. H.; Siegel, J. S. J. Am. Chem. Soc., in press.
29. 3): δ 35.6, 126.2, 126.6, 127.7, 127.9, 129.9, 131.25, 131.28, 135.5, 135.6, 135.8, 136.4. HRMS: actual 433.9314 calcd 433.9306.
30. 11Br) 342.0029.
31. For methodological precedence, see: Grigg, R.; Teasdale, A.; Sridharan, V. Tetrahedron Lett. 1991, 32, 3859-3862.
32. Sygula, A.; Abdourazak, A. H.; Rabideau, P. W. J. Am. Chem. Soc. 1996, 118, 339-343.