A strain-releasing trap for highly reactive electrophiles: Structural characterization of bowl-shaped arenium carbocations

Angewandte Chemie - International Edition

Volumn 50, Issue 13, 2011, Pages 2971-2974

  Zabula, Alexander V ^a   Spisak, Sarah N ^a   Filatov, Alexander S ^a   Rogachev, Andrey Yu ^b   Petrukhina, Marina A ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Carbocations; Corannulenes; Density functional calculations; Electrophilic addition; Structure elucidation

Indexed keywords

CARBOCATIONS; CORANNULENES; DENSITY FUNCTIONAL CALCULATIONS; ELECTROPHILIC ADDITIONS; STRUCTURE ELUCIDATION;

HYDROCARBONS; X RAY DIFFRACTION;

DENSITY FUNCTIONAL THEORY;

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC; STEREOISOMERISM;

EID: 79952656167     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201007762     Document Type: Article

References (30)

1. For reviews, see: a) P.W. Rabideau, A. Sygula, Acc. Chem. Res. 1996, 29, 235-242;
2. b) V. M. Tsefrikas, L. T. Scott, Chem. Rev. 2006, 106, 4868-4884;
3. c) Y.-T.Wu, J. S. Siegel, Chem. Rev. 2006, 106, 4843-4867;
4. d) A. S. Filatov, M. A. Petrukhina, Coord. Chem. Rev. 2010, 254, 2234-2246.
5. a) T. J. Seiders, E. L. Elliott, G. H. Grube, J. S. Siegel, J. Am. Chem. Soc. 1999, 121, 7804-7813;
6. b) G. Xu, A. Sygula, Z. Marcinow, P.W. Rabideau, Tetrahedron Lett. 2000, 41, 9931-9934;
7. c) H. B. Lee, P. R. Sharp, Organometallics 2005, 24, 4875-4877;
8. d) T. Amaya, T. Nakata, T. Hirao, J. Am. Chem. Soc. 2009, 131, 10810-10811;
9. e) R. Maag, B. H. Northrop, A. Butterfield, A. Linden, O. Zerbe, Y. M. Lee, K.-W. Chi, P. J. Stang, J. S. Siegel, Org. Biomol. Chem. 2009, 7, 4881-4885;
10. f) B. D. Steinberg, E. A. Jackson, A. S. Filatov, A. Wakamiya, M. A. Petrukhina, L. T. Scott, J. Am. Chem. Soc. 2009, 131, 10537-10545.
11. A. Yu. Rogachev, M. A. Petrukhina, J. Phys. Chem. A 2009, 113, 5743-5753.
12. D. V. Preda, L. T. Scott, Tetrahedron Lett. 2000, 41, 9633-9637.
13. L. T. Scott, H. E. Bronstein, D. V. Preda, R. B. M. Ansems, M. S. Bratcher, S. Hagen, Pure Appl. Chem. 1999, 71, 209-219.
14. a) T. Kitagawa, H. Sakamoto, K. Takeuchi, J. Am. Chem. Soc. 1999, 121, 4298-4299;
15. b) T. Kitagawa, Y. Lee, N. Masaoka, K. Komatsu, Angew. Chem. 2005, 117, 1422-1425;
16. Angew. Chem. Int. Ed. 2005, 44, 1398-1401.
17. M. Riccò, D. Pontiroli, M. Mazzani, F. Gianferrari, M. Pagliari, A. Goffredi, M. Brunelli, G. Zandomeneghi, B. H. Meier, T. Shiroka, J. Am. Chem. Soc. 2010, 132, 2064-2068.
18. See the Supporting Information for detailed synthetic procedures, characterization, X-ray diffraction study, and DFT calculations.
19. a) J. C. Hanson, C. E. Nordman, Acta Crystallogr. Sect. B 1976, 32, 1147-1153;
20. b) M. A. Petrukhina, K.W. Andreini, J. Mack, L. T. Scott, J. Org. Chem. 2005, 70, 5713-5716.
21. A. S. Filatov, L. T. Scott, M. A. Petrukhina, Cryst. Growth Des. 2010, 10, 4607-4621.
22. a) T. Amaya, H. Sakane, T. Hirao, Angew. Chem. 2007, 119, 8528-8531;
23. Angew. Chem. Int. Ed. 2007, 46, 8376-8379;
24. b) B. L. Schottel, H. T. Chifotides, K. R. Dunbar, Chem. Soc. Rev. 2008, 37, 68-83.
25. a) C. A. Reed, K.-C. Kim, R. D. Bolskar, L. J. Mueller, Science 2000, 289, 101-104;
26. b) L. J. Mueller, D. W. Elliott, G. M. Leskowitz, J. Struppe, R. A. Olsen, K.-C. Kim, C. A. Reed, J. Magn. Reson. 2004, 168, 327-335.
27. A. Ueda, S. Nishida, K. Fukui, T. Ise, D. Shiomi, K. Sato, T. Takui, K. Nakasuji, Y. Morita, Angew. Chem. 2010, 122, 1722-1726;
28. Angew. Chem. Int. Ed. 2010, 49, 1678-1682.
29. a) H. E. Bronstein, L. T. Scott, J. Org. Chem. 2008, 73, 88-93;
30. b) A. S. Filatov, A. Yu. Rogachev, E. A. Jackson, L. T. Scott, M. A. Petrukhina, Organometallics 2010, 29, 1231-1237.