π-strain-induced electrophilicity in small cycloalkynes: A DFT analysis of the polar cycloaddition of cyclopentyne towards enol ethers

European Journal of Organic Chemistry

Volumn , Issue 2, 2006, Pages 498-506

  Domingo, Luis R ^a   Pérez, Patricia ^b,c   Contreras, Renato ^c  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSIDAD ANDRÉS BELLO   (Chile)

^c UNIVERSITY OF CHILE   (Chile)

Author keywords

Cycloadditions; Cycloalkynes; Density functional calculations; Electrophilicity; Strain

Indexed keywords

EID: 31144457539     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500466     Document Type: Article

References (45)

1. L. Fitjer, S. Modaressi, Tetrahedron Lett. 1983, 24, 5495.
2. J. C. Gilbert, M. E. Baze, J. Am. Chem. Soc. 1984, 106, 1885.
3. R. B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Weinheim, 1970.
4. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, John Wiley & Sons, New York, 1976.
5. S. M. Bachrach, J. C. Gilbert, D. W. Laird, J. Am. Chem. Soc. 2001, 123, 6706.
6. D. W. Laird, J. C. Gilbert, J. Am. Chem. Soc. 2001, 123, 6704.
7. J. C. Gilbert, D.-R. Hou, J. Org. Chem. 2003, 68, 10067.
8. R. Huisgen, H. Rist, Justus Liebigs Ann. Chem. 1955, 594, 137.
9. R. A. Benkeser, C. E. DeBoer, J. Org. Chem. 1956, 21, 281.
10. T. Matsumoto, T. Hosoya, M. Katsuki, K. Suzuki, Tetrahedron Lett. 1991, 32, 6735.
11. T. Hosoya, T. Hasegawa, Y. Kuriyama, T. Matsumoto, K. Suzuki, Synlett 1995, 177.
12. T. Hosoya, T. Hasegawa, Y. Kuriyama, K. Suzuki, Tetrahedron Lett. 1995, 36, 3377.
13. T. Hosoya, T. Hamura, Y. Kuriyama, K. Suzuki, Synlett 2000, 520.
14. T. Hamura, T. Hosoya, H. Yamaguchi, Y. Kuriyama, M. Tanabe, M. Miyamoto, Y. Yasui, T. Matsumoto, K. Suzuki, Helv. Chim. Acta 2002, 85, 3589.
15. T. Hamura, Y. Ibusuki, K. Sato, T. Matsumoto, Y. Osamura, K. Suzuki, Org. Lett. 2003, 5, 3551.
16. S. M. Bachrach, J. C. Gilbert, J. Org. Chem. 2004, 69, 6357.
17. I. Ozkan, A. Kinal, J. Org. Chem. 2004, 69, 5390.
18. L. R. Domingo, M. Arnó, J. Andrés, J. Org. Chem. 1999, 64, 5867.
19. L. R. Domingo, Tetrahedron 2002, 58, 3765.
20. L. R. Domingo, M. J. Aurell, P. Pérez, R. Contreras, J. Org. Chem. 2003, 68, 3884.
21. R. G. Parr, L. von Szentpaly, S. Liu, J. Am. Chem. Soc. 1999, 121, 1922.
22. L. R. Domingo, M. J. Aurell, P. Pérez, R. Contreras, Tetrahedron 2002, 58, 4417.
23. P. Pérez, L. R. Domingo, M. J. Aurell, R. Contreras, Tetrahedron 2003, 59, 3117.
24. J. A. Sáez, M. Arnó, L. R. Domingo, Org. Lett. 2003, 5, 4117.
25. L. R. Domingo, P. Pérez, R. Contreras, Lett. Org. Chem. 2005, 2, 68.
26. R. P. Johnson, K. J. Daoust, J. Am. Chem. Soc. 1995, 117, 362.
27. G. S. Hammond, J. Am. Chem. Soc. 1955, 77, 334.
28. L. R. Domingo, J. Org. Chem. 2001, 66, 3211.
29. R. G. Parr, W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
30. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
31. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
32. W. J. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab initio Molecular Orbital Theory, Wiley, New York, 1986.
33. H. B. Schlegel, J. Comput. Chem. 1982, 3, 214.
34. H. B. Schlegel, Geometry Optimization on the Potential Energy Surface, in Modern Electronic Structure Theory (Ed.: D. R. Yarkony), World Scientific Publishing, Singapore, 1994.
35. K. Fukui, J. Phys. Chem. 1970, 74, 4161.
36. C. González, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523.
37. C. González, H. B. Schlegel, J. Chem. Phys. 1991, 95, 5853.
38. A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys. 1985, 83, 735.
39. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.
40. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.6, Gaussian, Inc., Pittsburgh, PA, 1998.
41. J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027.
42. B. Y. Simkin, I. Sheikhet, Quantum Chemical and Statistical Theory of Solutions - A Computational Approach, Ellis Horwood, London, 1995.
43. M. Cossi, V. Barone, R. Cammi, J. Tomasi, Chem. Phys. Lett. 1996, 255, 327.
44. E. Cances, B. Mennuncci, J. Tomasi, J. Chem. Phys. 1997, 107, 3032.
45. V. Barone, M. Cossi, J. Tomasi, J. Comp. Chem. 1998, 19, 404.