Ab initio and density functional calculations on the pericyclic vs pseudopericyclic mode of conjugated nitrile ylide 1,5-electrocyclizations

Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 47-53

  Fabian, Walter M F ^a   Kappe, C Oliver ^a   Bakulev, Vasiliy A ^b  

^a UNIVERSITY OF GRAZ   (Austria)

^b URAL FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; NITRILE; NITROGEN DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; CYCLIZATION; MATHEMATICAL COMPUTING; REACTION ANALYSIS;

EID: 0033958546     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990997s     Document Type: Article

References (72)

1. (a) Huisgen, R.; Stangl, H.; Sturm, H. J.; Raab, R.; Bunge, K. Chem. Ber. 1972, 105, 1258.
2. (b) Huisgen, R.; Stangl, H.; Sturm, H. J.; Wagenhofer, H. Angew. Chem., Int. Ed. Engl. 1962, 1, 50.
3. (c) Engel, N.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 676.
4. (d) Padwa, A.; Smolanoff, J.; Tremper, A. J. Am. Chem. Soc. 1975, 97, 4682.
5. (e) Padwa, A.; Smolanoff, J.; Tremper, A. J. Org. Chem. 1976, 41, 543.
6. (f) Singh, B.; Ullman, E. F. J. Am. Chem. Soc. 1967, 89, 6911.
7. (g) Singh, B.; Zweig, A.; Gallivan, J. B. J. Am. Chem. Soc. 1972, 94, 1199.
8. (h) Batori, S.; Döpp, D.; Messmer, A. Tetrahedron 1994, 50, 4699.
9. (i) Wipf, P.; Prewo, R.; Bieri, J. H.; Germain, G.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 1177.
10. (j) Bozhkova, N.; Heimgartner, H. Helv. Chim. Acta 1989, 72, 825.
11. (k) Gruber, P.; Müller, L.; Steglich, W. Chem. Ber. 1973, 106, 2863.
12. (l) Huisgen, R.; König, H.; Binsch, G.; Sturm, H. J. Angew. Chem. 1961, 73, 368.
13. (m) Huisgen, R.; Binsch, G.; Ghosez, L. Chem. Ber. 1964, 97, 2628.
14. (n) Huisgen, R.; Sturm, H. J.; Binsch, G. Chem. Ber. 1964, 97, 2864.
15. (o) Kende, A. S.; Hebeisen, P.; Sanfilippo, P. J.; Toder, B. H. J. Am. Chem. Soc. 1982, 104, 4244.
16. (p) Janulis, E. P., Jr.; Wilson, S. R.; Arduengo, A. J. Tetrahedron Lett. 1984, 25, 405.
17. (q) Padwa, A.; Gasdaska, J. R.; Tomas, M.; Turro, N. J.; Cha, Y.; Gould, I. R. J. Am. Chem. Soc. 1986, 108, 6739.
18. (r) Wentrup, C.; Berstermann, H. M.; Burger, K.; Fischer, S.; Kuzaj, M.; Luerssen, H. Angew. Chem., Int. Ed. Engl. 1986, 25, 85.
19. (a) Fukushima, K.; Ibata, T. Heterocycles 1995, 40, 149.
20. (b) Fukushima, K.; Ibata, T. Bull. Chem. Soc. Jpn. 1995, 68, 3469.
21. (c) Fukushima, K.; Lu, Y.-Q.; Ibata, T. Bull. Chem. Soc. Jpn. 1996, 69, 3289.
22. (d) Beall, L. S.; Padwa, A. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press: Greenwich, CT, 1998; Vol. 3, pp 117-158.
23. (a) Bojkova, N.; Heimgartner, H. Heterocycles 1998, 47, 781.
24. (b) Hansen, H.-J.; Heimgartner, H. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, p 177.
25. (c) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 1081.
26. (d) Claus, P. K. In Houben-Weyl, Methoden der Organischen Chemie; Klamann, D., Hagemann, H., Eds.; G. Thieme Verlag: Stuttgart, 1990; Vol. E14b, p 3.
27. (a) Turchi, I. J.; Dewar, M. J. S. Chem. Rev. 1975, 75, 389.
28. (b) Taylor, E. C.; Turchi, I. J. Chem. Rev. 1979, 79, 181.
29. (c) Benincori, T.; Brenna, E.; Sannicolo, F. J. Chem. Soc., Perkin Trans. 1 1993, 675.
30. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 947.
31. (a) Zecchi, G. Synthesis 1991, 181.
32. (b) Cullen, K. E.; Sharp, J. T. J. Chem. Soc., Perkin Trans. 1 1995, 2565.
33. (c) Strachan, J.-P.; Sharp, J. T.; Parsons, S. J. Chem. Soc., Perkin Trans. 1 1998, 807.
34. Snyder, J. P. J. Org. Chem. 1980, 45, 1341.
35. (a) Bakulev, V. A.; Gloriozov, I. P. Khim. Geterotsikl. Soedin. 1989, 504.
36. (b) Bakulev, V. A.; Morzherin, Y. Yu.; Lebedev, A. T.; Dankova, E. F.; Kolobov, M. Yu.; Shafran, Y, M. Bull. Soc. Chim. Belg. 1993, 102, 493.
37. (c) Bakulev, V. A. Russ. Chem. Rev. 1995, 64, 99.
38. (d) Bakulev, V. A.; Biritschowa, N.; Pitschko, V. A. Khim. Geterotsikl. Soedin. 1997, 113.
39. (e) Bakulev, V. A.; Kappe, C. O.; Padwa, A. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 149-229.
40. Ross, J. A.; Seiders, R. P.; Lemal, D. M. J. Am. Chem. Soc. 1976, 98, 4325.
41. For a critique concerning the term "pseudopericyclic", see: Snyder, J. P.; Halgren, T. A. J. Am. Chem. Soc. 1980, 102, 2861.
42. (a) Burke, L. A.; Elguero, J.; Leroy, G.; Sana, M. J. Am. Chem. Soc. 1976, 98, 1685.
43. (b) Burke, L. A.; Leroy, G.; Nguyen, M. T.; Sana, M. J. Am. Chem. Soc. 1978, 100, 3668.
44. (a) Birney, D. M.; Wagenseller, P. E. J. Am. Chem. Soc. 1994, 116, 6262.
45. (b) Wagenseller, P. E.; Birney, D. M.; Roy, D. J. Org. Chem. 1995, 60, 2853.
46. (c) Birney, D. M. J. Org. Chem. 1996, 61, 243.
47. (d) Birney, D. M.; Ham, S.; Unruh, G. R. J. Am. Chem. Soc. 1997, 119, 4509.
48. (e) Birney, D. M.; Xu, X.; Ham, S.; Huang, X. J. Org. Chem. 1997, 62, 7114.
49. (f) Birney, D. M.; Xu, X. L.; Ham, S. Angew. Chem., Int. Ed. Engl. 1999, 38, 189.
50. (g) Quideau, S.; Looney, M. A.; Pouysegu, L.; Ham, S.; Birney, D. M. Tetrahedron Lett. 1999, 40, 615.
51. (a) Eisenberg, S. W. E.; Kurth, M. J.; Fink, W. H. J. Org. Chem. 1995, 60, 3736.
52. (b) Morao, I.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1997, 62, 7033
53. (c) Luo, L.; Bartberger, M. D.; Dolbier, W. R., Jr. J. Am. Chem. Soc. 1997, 119, 12366.
54. (d) Morales-Rios, M. S.; Suarez-Castillo, O. R.; Garcia-Martinez, C.; Joseph-Nathan, P. Synthesis 1998, 1755.
55. Liu, R. C. Y.; Lusztyk, J.; McAllister, M. A.; Tidwell, T. T.; Wagner, B. D. J. Am. Chem. Soc. 1998, 120, 6247.
56. Koch, R.; Wong, M. W.; Wentrup, C. J. Org. Chem. 1996, 61, 6809.
57. Fabian, W. M. F.; Bakulev, V. A.; Kappe, C. O. J. Org. Chem. 1998, 63, 5801.
58. Cornforth, J. W. In The Chemistry of Penicillin; Princeton University Press: Princeton, 1949.
59. (a) Dewar, M. J. S.; Turchi, I. J. J. Am. Chem. Soc. 1974, 96, 6148.
60. (b) Dewar, M. J. S.; Turchi, I. J. J. Org. Chem. 1975, 40, 1521.
61. (c) Dewar, M. J. S.; Turchi, I. J. J. Chem. Soc., Perkin Trans. 2 1977, 724.
62. (d) Corrao, S. L.; Macielag, M. J.; Turchi, I. J. J. Org. Chem. 1990, 55, 4484.
63. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr. 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.; 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.3. Gaussian, Inc., Pittsburgh, PA, 1998.
64. (a) Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
65. (b) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 281.
66. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
67. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
68. Reed, A. D.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
69. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1; Madison, WI, 1988.
70. Saalfrank, R. W.; Lurz, C.-J.; Hassa, J.; Danion, D.; Toupet, L. Chem. Ber. 1991, 124, 595.
71. Houk, K. N.; Yamaguchi, K. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 2, p 407.
72. Jiao, H.; Schleyer, P. v. R. J. Phys. Org. Chem. 1998, 11, 655.