Quantitative characterization of the global electrophilicity pattern of some reagents involved in 1,3-dipolar cycloaddition reactions

Tetrahedron

Volumn 59, Issue 17, 2003, Pages 3117-3125

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

^a UNIVERSIDAD ANDRÉS BELLO   (Chile)

^b UNIVERSITY OF VALENCIA   (Spain)

^c UNIVERSITY OF CHILE   (Chile)

Author keywords

1,3 dipolar cycloadditions; Density functional theory; Electrophilicity power

Indexed keywords

AZIDE; NITRILE; NITRONE; OXIDE;

ARTICLE; CYCLOADDITION; DIPOLE; ELECTRON; EVALUATION; MOLECULE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS;

BETULACEAE;

EID: 0037459857     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00374-0     Document Type: Article

References (46)

1. (a) Padwa A. 1,3-Dipolar Cycloaddition Chemistry. Vols. 1-2:1984;Wiley/Interscience, New York.
2. (b) Padwa A. Trost B.M., Fleming I. Comprehensive Organic Chemistry. Vol. 4:1991;1069-1109 Pergamon, Oxford.
3. Wasserman A. Diels-Alder Reactions. 1965;Elsevier, New York.
4. Fleming I. Pericyclic Reactions. 1999;Oxford University, Oxford.
5. (a) Huisgen R. Angew. Chem. Int. Ed. Engl. 6:1967;16 (b) Huisgen R., Grashey R., Sauer J. Patai S. The Chemistry of Alkenes. 1964;739 Interscience, New York.
6. (a) Huisgen R. Angew. Chem. Int. Ed. Engl. 6:1967;16 (b) Huisgen R., Grashey R., Sauer J. Patai S. The Chemistry of Alkenes. 1964;739 Interscience, New York.
7. (a) Gothelf K.V., Jorgensen K.A. Chem. Rev. 98:1998;863 (b) Gothelf K.V. Kobayashi S., Jorgensen K.A. Asymmetric Metal-Catalysed 1,3-Dipolar Cycloaddition Reactions. 2001;211-248 Wiley/VCH, Weinheim.
8. (a) Gothelf K.V., Jorgensen K.A. Chem. Rev. 98:1998;863 (b) Gothelf K.V. Kobayashi S., Jorgensen K.A. Asymmetric Metal-Catalysed 1,3-Dipolar Cycloaddition Reactions. 2001;211-248 Wiley/VCH, Weinheim.
9. Huisgen R. Padwa A. 1,3-Dipolar Cycloadditions Chemistry. Vol. 1:1984;Wiley, New York.
10. (a) Huisgen R. J. Org. Chem. 33:1968;2291 (b) Huisgen R. J. Org. Chem. 41:1976;1976.
11. (a) Huisgen R. J. Org. Chem. 33:1968;2291 (b) Huisgen R. J. Org. Chem. 41:1976;1976.
12. (a) Firestone R.A. J. Org. Chem. 33:1968;2285 (b) Firestone R.A. J. Org. Chem. 37:1972;2181.
13. (a) Firestone R.A. J. Org. Chem. 33:1968;2285 (b) Firestone R.A. J. Org. Chem. 37:1972;2181.
14. Huisgen R., Mloston G., Langhals E. Helv. Chim. Acta. 84:2001;1805.
15. Huisgen R., Mloston G., Langhals E. J. Org. Chem. 51:1986;4087.
16. Rostovtsev V.V., Green L.G., Fokin V.V., Sharpless K.B. Angew. Chem. Int. Ed. 41:2001;2596.
17. (a) Sustmann R., Shubert R. Tetrahedron Lett. 1972;2739 (b) Sustmann R., Trill H. Tetrahedron Lett. 1972;4271 (c) Sustmann R. Pure Appl. Chem. 40:1974;569.
18. (a) Sustmann R., Shubert R. Tetrahedron Lett. 1972;2739 (b) Sustmann R., Trill H. Tetrahedron Lett. 1972;4271 (c) Sustmann R. Pure Appl. Chem. 40:1974;569.
19. (a) Sustmann R., Shubert R. Tetrahedron Lett. 1972;2739 (b) Sustmann R., Trill H. Tetrahedron Lett. 1972;4271 (c) Sustmann R. Pure Appl. Chem. 40:1974;569.
20. Kuczkowski R.L. Padwa A. 1,3-Dipolar Cycloaddition Chemistry. 1984;197 Wiley/Interscience, New York.
21. (a) Gothelf K.V., Hazell R.G., Jorgensen K.A. J. Org. Chem. 61:1996;346 (b) Tanaka K., Imase T., Iwata S. Bull. Chem. Soc. Jpn. 69:1996;2243 (c) Morao I., Lecea B., Cossío F.P. J. Org. Chem. 62:1997;7033 (d) Liu J., Niwayama S., You Y., Houk K.N. J. Org. Chem. 63:1998;1064 (e) Magnusong E.C., Pranata J. J. Comput. Chem. 19:1998;1795 (f) Cossío F.P., Morao I., Jiao H., Scheleyer P., Von R. J. Am. Chem. Soc. 121:1999;6737 (g) Carda M., Portolés R., Murga J., Uriel S., Marco J.A., Domingo L.R., Zaragozá J.R., Röper H. J. Org. Chem. 65:2000;7000 (h) Tanaka J., Kanemasa S. Tetrahedron. 57:2001;899 (i) Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry. 13:2002;173.
22. (a) Gothelf K.V., Hazell R.G., Jorgensen K.A. J. Org. Chem. 61:1996;346 (b) Tanaka K., Imase T., Iwata S. Bull. Chem. Soc. Jpn. 69:1996;2243 (c) Morao I., Lecea B., Cossío F.P. J. Org. Chem. 62:1997;7033 (d) Liu J., Niwayama S., You Y., Houk K.N. J. Org. Chem. 63:1998;1064 (e) Magnusong E.C., Pranata J. J. Comput. Chem. 19:1998;1795 (f) Cossío F.P., Morao I., Jiao H., Scheleyer P., Von R. J. Am. Chem. Soc. 121:1999;6737 (g) Carda M., Portolés R., Murga J., Uriel S., Marco J.A., Domingo L.R., Zaragozá J.R., Röper H. J. Org. Chem. 65:2000;7000 (h) Tanaka J., Kanemasa S. Tetrahedron. 57:2001;899 (i) Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry. 13:2002;173.
23. (a) Gothelf K.V., Hazell R.G., Jorgensen K.A. J. Org. Chem. 61:1996;346 (b) Tanaka K., Imase T., Iwata S. Bull. Chem. Soc. Jpn. 69:1996;2243 (c) Morao I., Lecea B., Cossío F.P. J. Org. Chem. 62:1997;7033 (d) Liu J., Niwayama S., You Y., Houk K.N. J. Org. Chem. 63:1998;1064 (e) Magnusong E.C., Pranata J. J. Comput. Chem. 19:1998;1795 (f) Cossío F.P., Morao I., Jiao H., Scheleyer P., Von R. J. Am. Chem. Soc. 121:1999;6737 (g) Carda M., Portolés R., Murga J., Uriel S., Marco J.A., Domingo L.R., Zaragozá J.R., Röper H. J. Org. Chem. 65:2000;7000 (h) Tanaka J., Kanemasa S. Tetrahedron. 57:2001;899 (i) Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry. 13:2002;173.
24. (a) Gothelf K.V., Hazell R.G., Jorgensen K.A. J. Org. Chem. 61:1996;346 (b) Tanaka K., Imase T., Iwata S. Bull. Chem. Soc. Jpn. 69:1996;2243 (c) Morao I., Lecea B., Cossío F.P. J. Org. Chem. 62:1997;7033 (d) Liu J., Niwayama S., You Y., Houk K.N. J. Org. Chem. 63:1998;1064 (e) Magnusong E.C., Pranata J. J. Comput. Chem. 19:1998;1795 (f) Cossío F.P., Morao I., Jiao H., Scheleyer P., Von R. J. Am. Chem. Soc. 121:1999;6737 (g) Carda M., Portolés R., Murga J., Uriel S., Marco J.A., Domingo L.R., Zaragozá J.R., Röper H. J. Org. Chem. 65:2000;7000 (h) Tanaka J., Kanemasa S. Tetrahedron. 57:2001;899 (i) Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry. 13:2002;173.
25. (a) Gothelf K.V., Hazell R.G., Jorgensen K.A. J. Org. Chem. 61:1996;346 (b) Tanaka K., Imase T., Iwata S. Bull. Chem. Soc. Jpn. 69:1996;2243 (c) Morao I., Lecea B., Cossío F.P. J. Org. Chem. 62:1997;7033 (d) Liu J., Niwayama S., You Y., Houk K.N. J. Org. Chem. 63:1998;1064 (e) Magnusong E.C., Pranata J. J. Comput. Chem. 19:1998;1795 (f) Cossío F.P., Morao I., Jiao H., Scheleyer P., Von R. J. Am. Chem. Soc. 121:1999;6737 (g) Carda M., Portolés R., Murga J., Uriel S., Marco J.A., Domingo L.R., Zaragozá J.R., Röper H. J. Org. Chem. 65:2000;7000 (h) Tanaka J., Kanemasa S. Tetrahedron. 57:2001;899 (i) Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry. 13:2002;173.
26. (a) Gothelf K.V., Hazell R.G., Jorgensen K.A. J. Org. Chem. 61:1996;346 (b) Tanaka K., Imase T., Iwata S. Bull. Chem. Soc. Jpn. 69:1996;2243 (c) Morao I., Lecea B., Cossío F.P. J. Org. Chem. 62:1997;7033 (d) Liu J., Niwayama S., You Y., Houk K.N. J. Org. Chem. 63:1998;1064 (e) Magnusong E.C., Pranata J. J. Comput. Chem. 19:1998;1795 (f) Cossío F.P., Morao I., Jiao H., Scheleyer P., Von R. J. Am. Chem. Soc. 121:1999;6737 (g) Carda M., Portolés R., Murga J., Uriel S., Marco J.A., Domingo L.R., Zaragozá J.R., Röper H. J. Org. Chem. 65:2000;7000 (h) Tanaka J., Kanemasa S. Tetrahedron. 57:2001;899 (i) Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry. 13:2002;173.
27. (a) Gothelf K.V., Hazell R.G., Jorgensen K.A. J. Org. Chem. 61:1996;346 (b) Tanaka K., Imase T., Iwata S. Bull. Chem. Soc. Jpn. 69:1996;2243 (c) Morao I., Lecea B., Cossío F.P. J. Org. Chem. 62:1997;7033 (d) Liu J., Niwayama S., You Y., Houk K.N. J. Org. Chem. 63:1998;1064 (e) Magnusong E.C., Pranata J. J. Comput. Chem. 19:1998;1795 (f) Cossío F.P., Morao I., Jiao H., Scheleyer P., Von R. J. Am. Chem. Soc. 121:1999;6737 (g) Carda M., Portolés R., Murga J., Uriel S., Marco J.A., Domingo L.R., Zaragozá J.R., Röper H. J. Org. Chem. 65:2000;7000 (h) Tanaka J., Kanemasa S. Tetrahedron. 57:2001;899 (i) Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry. 13:2002;173.
28. (a) Gothelf K.V., Hazell R.G., Jorgensen K.A. J. Org. Chem. 61:1996;346 (b) Tanaka K., Imase T., Iwata S. Bull. Chem. Soc. Jpn. 69:1996;2243 (c) Morao I., Lecea B., Cossío F.P. J. Org. Chem. 62:1997;7033 (d) Liu J., Niwayama S., You Y., Houk K.N. J. Org. Chem. 63:1998;1064 (e) Magnusong E.C., Pranata J. J. Comput. Chem. 19:1998;1795 (f) Cossío F.P., Morao I., Jiao H., Scheleyer P., Von R. J. Am. Chem. Soc. 121:1999;6737 (g) Carda M., Portolés R., Murga J., Uriel S., Marco J.A., Domingo L.R., Zaragozá J.R., Röper H. J. Org. Chem. 65:2000;7000 (h) Tanaka J., Kanemasa S. Tetrahedron. 57:2001;899 (i) Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry. 13:2002;173.
29. (a) Gothelf K.V., Hazell R.G., Jorgensen K.A. J. Org. Chem. 61:1996;346 (b) Tanaka K., Imase T., Iwata S. Bull. Chem. Soc. Jpn. 69:1996;2243 (c) Morao I., Lecea B., Cossío F.P. J. Org. Chem. 62:1997;7033 (d) Liu J., Niwayama S., You Y., Houk K.N. J. Org. Chem. 63:1998;1064 (e) Magnusong E.C., Pranata J. J. Comput. Chem. 19:1998;1795 (f) Cossío F.P., Morao I., Jiao H., Scheleyer P., Von R. J. Am. Chem. Soc. 121:1999;6737 (g) Carda M., Portolés R., Murga J., Uriel S., Marco J.A., Domingo L.R., Zaragozá J.R., Röper H. J. Org. Chem. 65:2000;7000 (h) Tanaka J., Kanemasa S. Tetrahedron. 57:2001;899 (i) Merino P., Mates J.A., Revuelta J., Tejero T., Chiacchio U., Romeo G., Iannazzo D., Romeo R. Tetrahedron: Asymmetry. 13:2002;173.
30. Kanemasa S., Ueno N., Shirahase M. Tetrahedron Lett. 43:2002;657.
31. (a) Seerden J.-P.G., Scholte op Reimer W.A., Scheeren H.W. Tetrahedron Lett. 35:1994;4419 (b) Seerden J.-P.G., Kuypers M.M.M., Scheeren H.W. Tetrahedron: Asymmetry. 6:1995;1441 (c) Seerden J.-P.G., Boeren M.M.M., Scheeren H.W. Tetrahedron. 53:1997;11842.
32. (a) Seerden J.-P.G., Scholte op Reimer W.A., Scheeren H.W. Tetrahedron Lett. 35:1994;4419 (b) Seerden J.-P.G., Kuypers M.M.M., Scheeren H.W. Tetrahedron: Asymmetry. 6:1995;1441 (c) Seerden J.-P.G., Boeren M.M.M., Scheeren H.W. Tetrahedron. 53:1997;11842.
33. (a) Seerden J.-P.G., Scholte op Reimer W.A., Scheeren H.W. Tetrahedron Lett. 35:1994;4419 (b) Seerden J.-P.G., Kuypers M.M.M., Scheeren H.W. Tetrahedron: Asymmetry. 6:1995;1441 (c) Seerden J.-P.G., Boeren M.M.M., Scheeren H.W. Tetrahedron. 53:1997;11842.
34. Simonsen K.B., Bayón P., Hazell R.G., Gothelf K.V., Jorgensen K.A. J. Am. Chem. Soc. 121:1999;3845.
35. Domingo L.R. Eur. J. Org. Chem. 2000;2265.
36. Parr R.G., Szentpály L.V., Liu S. J. Am. Chem. Soc. 121:1999;1922.
37. Domingo L.R., Aurell M.J., Pérez P., Contreras P. Tetrahedron. 48:2002;4417.
38. (a) Domingo L.R., Arnó M., Contreras R., Pérez P. J. Phys. Chem. A. 106:2002;952 (b) Domingo L.R., Aurell M.J. J. Org. Chem. 67:2002;959 (c) Domingo L.R. Tetrahedron. 58:2002;3765 (d) Domingo L.R., Asensio A., Arroyo P. J. Phys. Org. Chem. 15:2002;660 (e) Domingo L.R., Zaragozá R.J., Williams R.M. J. Org. Chem. 2003;. in press.
39. (a) Domingo L.R., Arnó M., Contreras R., Pérez P. J. Phys. Chem. A. 106:2002;952 (b) Domingo L.R., Aurell M.J. J. Org. Chem. 67:2002;959 (c) Domingo L.R. Tetrahedron. 58:2002;3765 (d) Domingo L.R., Asensio A., Arroyo P. J. Phys. Org. Chem. 15:2002;660 (e) Domingo L.R., Zaragozá R.J., Williams R.M. J. Org. Chem. 2003;. in press.
40. (a) Domingo L.R., Arnó M., Contreras R., Pérez P. J. Phys. Chem. A. 106:2002;952 (b) Domingo L.R., Aurell M.J. J. Org. Chem. 67:2002;959 (c) Domingo L.R. Tetrahedron. 58:2002;3765 (d) Domingo L.R., Asensio A., Arroyo P. J. Phys. Org. Chem. 15:2002;660 (e) Domingo L.R., Zaragozá R.J., Williams R.M. J. Org. Chem. 2003;. in press.
41. (a) Domingo L.R., Arnó M., Contreras R., Pérez P. J. Phys. Chem. A. 106:2002;952 (b) Domingo L.R., Aurell M.J. J. Org. Chem. 67:2002;959 (c) Domingo L.R. Tetrahedron. 58:2002;3765 (d) Domingo L.R., Asensio A., Arroyo P. J. Phys. Org. Chem. 15:2002;660 (e) Domingo L.R., Zaragozá R.J., Williams R.M. J. Org. Chem. 2003;. in press.
42. (a) Domingo L.R., Arnó M., Contreras R., Pérez P. J. Phys. Chem. A. 106:2002;952 (b) Domingo L.R., Aurell M.J. J. Org. Chem. 67:2002;959 (c) Domingo L.R. Tetrahedron. 58:2002;3765 (d) Domingo L.R., Asensio A., Arroyo P. J. Phys. Org. Chem. 15:2002;660 (e) Domingo L.R., Zaragozá R.J., Williams R.M. J. Org. Chem. 2003;. in press.
43. Parr R.G., Yang W. Density Functional Theory of Atoms and Molecules. 1989;Oxford University, New York.
44. Parr R.G., Pearson R.G. J. Am. Chem. Soc. 105:1983;7512.
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. J. A.; 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.; W. Gill; P. M.; 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.
46. Elender K., Riebel P., Weber A., Sauer J. Tetrahedron. 56:2000;4261.