A density functional theory study of rhodium-catalyzed hetero-[5+2]- cycloaddition of cyclopropyl imine derivatives and alkynes

Journal of Physical Chemistry A

Volumn 112, Issue 38, 2008, Pages 9068-9074

  Montero Campillo, M Merced ^a   Cabaleiro Lago, Enrique M ^b   Rodríguez Otero, Jesús ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b Facultade de Ciencias   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; HYDROCARBONS; NITROGEN COMPOUNDS; PROBABILITY DENSITY FUNCTION; RHODIUM; RHODIUM COMPOUNDS;

A-DENSITY; CYCLOPROPYL; IMINE DERIVATIVES; RHODIUM-CATALYZED;

DENSITY FUNCTIONAL THEORY;

EID: 53849107816     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp803785e     Document Type: Article

References (24)

1. A complete compilation of rhodium-catalyzed reactions can be founded in Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: New York, 2005.
2. Osborn, J. A.; Jardine, F. H; Young, J. F.; Wilkinson, G. J. Chem. Soc. A 1966, 1711.
3. See, for example, Wender, P. A.; Deschamps, N. M.; Sun, R. Angew. Chem. Int. Ed 2006, 45, 3957-3960, and references therein.
4. See, for example, Wender, P. A.; Gamber, G. G.; Hubbard, R. D; Zhang, L J. Am. Chem. Soc. 2002, 124, 2876.
5. "Cycloadditions are usually described as pericyclic reactions. However, not all cycloadditions are pericyclic. When in a cycloaddition charged or radical intermediates are involved or when the cycloadditionresult is obtained in a series of reactions steps, they are sometimes called 'formal cycloadditions'." (Extracted from Pericyclic Reactions; Fleming, I., Ed; Oxford Univeristy Press: Oxford, 1999.
6. Yu, Z.-X.; Wender, P. A.; Houk, K. N. J. Am. Chem. Soc. 2004, 126, 9154-9155.
7. O'Hagan, D. Nat. Prod. Rep. 1997, 14, 637-651.
8. Wender, P. A.; Pedersen, T. M; Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124, 15154-15155.
9. (a) Experimental reasons founded in some [5+2]-cycloadditions leed the authors of (8) to think that the most probable mechanism is (a) Kamitani, A; Chatani, N; Morimoto, T; Murai, S J. Org. Chem. 2000, 65, 9230-9233.
10. (b) Wender, P. A.; Takahashi, H; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721.
11. (c) Wender, P. A.; Rieck, H; Fuji, M J. Am Chem. Soc. 1998, 120, 10976-10977.
12. (a) Oxepines are present in natural products of biological interest Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251.
13. (b) Faulkner, D. J. Nat. Prod. Rep. 1986, 3, 1.
14. (c) Faulkner, D. J. Nat. Prod. Rep. 1988, 5, 613.
15. (a) Lee, C; Yang, W; Parr., R. J. Phys. Rev. B 1988, 37, 785.
16. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
17. Hay, P. J.; Wadt, W. R J. Chem. Phys. 1985, 82, 299.
18. (a) Fukui, K. Acc. Chem. Res. 1981, 14, 363.
19. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1989, 90, 2154.
20. (c) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5223.
21. Frisch, M. J.; Trucks, G. W. ; Schlegel, H. B.; Scuseria, G. E ; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T. ; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K. ; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M. ; Li, X.; Knox, J. E.; Hratchian, H. P. ; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E. ; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W. Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P. Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O; Malick, D. K.; Rabuck, A. D.; Raghavachari, K; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I; Martin, R. L.; Fox, D. J. Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.01; Gaussian, Inc.: Wallingford, CT, 2004.
22. See, for example, Wilson, M. R.; Prock, A.; Giering, W. P. Organometallics 2002, 21, 2758.
23. The VCP calculations are done with 6-31G(d) base for Cl, O, H, C atoms instead of die 6-31G(d,p) base used in this work; however, the comparison is still valid.
24. Zora, M. J. Org. Chem. 2005, 70, 6018-6026. and references therein.