Peri-, site-, and regioselectivity in heterocumulene-heterodiene cycloaddition reactions: An ab initio study of the system ketenimine + acrolein

Journal of the American Chemical Society

Volumn 119, Issue 18, 1997, Pages 4253-4257

  Fabian, Walter M F ^a   Janoschek, Rudolf ^b  

^a UNIVERSITY OF GRAZ   (Austria)

^b UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN;

ANALYTIC METHOD; ARTICLE; GENE REARRANGEMENT; GEOMETRY; KINETICS; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 0030907859     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963941d     Document Type: Article

References (48)

1. (a) Staudinger, H. Die Ketene; Enke: Stuttgart, 1912.
2. (b) Borrmann, D. In Houben-Weyl, 4th ed.; Müller, E., Ed.; Thieme: Stuttgart, 1968; Vol. 7/4, pp 53-447.
3. (c) Patai, S. The Chemistry of Ketenes, Allenes and Related Compounds; Wiley; New York, 1980.
4. (d) Ulrich, H. Cycloaddition Chemistry of Heterocumulenes; Academic Press; New York, 1967.
5. (a) Tidwell, T. T. Acc. Chem. Res. 1990, 23, 273-279.
6. (b) Tidwell, T. T. Ketenes; Wiley: New York, 1995.
7. (c) Allen, A. D.; Ma, J. H.; McAllister, M. A.; Tidwell, T. T.; Zhao, D. C. Acc. Chem. Res. 1995, 28, 265-271.
8. (a) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley London, 1976; pp 143-146.
9. (b) Huisgen, R.; Otto, P. Tetrahedron Lett. 1968, 43, 4491-4495.
10. (c) Huisgen, R.; Otto, P. J. Am. Chem. Soc. 1969, 91, 5922-5923.
11. (a) Bernardi, F.; Bottoni, A.; Robb, M. A.; Venturini, A. J. Am. Chem. Soc. 1990, 112, 2106-2114.
12. (b) Wang, X.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 1754-1756.
13. (c) Yamabe, S.; Minato, T.; Osamura, Y. J. Chem. Soc., Chem. Commun. 1993, 450-452.
14. (d) Bertran, J.; Oliva, A.; Jose, J.; Duran, M.; Molina, P.; Alajarin, M.; Leonardo, C. L.; Elguero, J. J. Chem. Soc., Perkin Trans. 2 1992, 299-304.
15. (e) Valenti, E.; Pericas, M. A.; Moyano, A. J. Org. Chem. 1990, 55, 3582-3593.
16. (f) Assfeld, X.; Ruiz-Lopez, M. F.; Gonzalez, J.; Lopez, R.; Sordo, J. A.; Sordo, T. L. J. Comput. Chem. 1994, 15, 479-487.
17. (g) Fang, D.-C.; Fu, X.-Y. Chin. J. Chem. 1996, 14, 97-104.
18. Lecea, B.; Arrastia, I.; Arrieta, A.; Roa, G.; Lopez, X.; Arriortua, M. I.; Ugalde, J. M.; Cossio, F. P. J. Org. Chem. 1996, 61, 3070-3079.
19. (a) Salzner, U.; Bachrach, S. M. J. Org. Chem. 1996, 61, 237-242.
20. (b) Seidl, E. T.; Schaefer, H. F., III J. Am. Chem. Soc. 1991, 113, 5195-5200.
21. (a) Mazumdar, S. N.; Mahajan, M. P. Tetrahedron 1991, 47, 1473-1484.
22. (b) Matsuda, I.; Yamamoto, S.; Ishii, Y. J. Chem. Soc., Perkin Trans. 1 1976, 1528-1532.
23. (c) Luthardt, P.; Würthwein, E. U. Tetrahedron Lett. 1988, 29, 921-924.
24. Desimoni, G.; Tacconi, G. Chem. Rev. 1975, 75, 651-692.
25. For a review, see: Wentrup, C.; Heilmayer, W.; Kollenz, G. Synthesis 1994, 25, 1219-1248.
26. (a) Eisenberg, S. W. E.; Kurth, M. J.; Fink, W. H. J. Org. Chem. 1995, 60, 3736-3742.
27. (b) Birney, D. M.; Wagenseller, P. E. J. Am. Chem. Soc. 1994, 116, 6262-6270.
28. (c) Wagenseller, P. E.; Birney, D. M.; Roy, D. J. Org. Chem. 1995, 60, 2853-2859.
29. (d) Birney, D. M. J. Org. Chem. 1996, 61, 243-251.
30. (e) Hong, S.-G.; Fu, X.-Y. J. Mol. Struct. (THEOCHEM) 1990, 209, 241-246.
31. Zhao, D.-C.; Tidwell, T. T. J. Am. Chem. Soc. 1992, 114, 10981-10983.
32. Pittol, C. A.; Roberts, S. M.; Sutton, P. W.; Williams, J. O. J. Chem. Soc., Chem. Commun. 1994, 803-804.
33. Yamabe, S.; Dai, T.; Minato, T.; Machiguchi, T.; Hasegawa, T. J. Am. Chem. Soc. 1996, 118, 6518-6519.
34. For a review, see: Kollenz, G.; Heilmayer, W. Trends Heterocycl. Chem. 1993, 3, 379-395.
35. (a) Kollenz, G.; Penn, G.; Ott, W.; Peters, K.; Peters, E.-M.; Schnering, H. G. Heterocycles 1987, 26, 625-631.
36. (b) Kollenz, G.; Sterk, H.; Hutter, G. J. Org. Chem. 1991, 56, 235-239.
37. L'abbe, G.; Dekerk, J. P.; Declerque, J. P.; Germain, G.; van Meersche, M. Tetrahedron Lett. 1979, 3213-3216.
38. Review: Dondoni, A. Heterocydes, 1980, 14, 1547-1566.
39. Gaussian 94, Revision B.3; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.
40. Pople, J. A.; Scott, A. P.; Wong, W. M.; Radom, L. Isr. J. Chem. 1993, 33, 345-350.
41. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
42. NBO Version 3.1; Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.; Wisconsin, 1988.
43. Fang, D.-C.; Fu, X.-Y. Chem. Phys. Lett. 1996, 259, 265-270.
44. (a) Singer, L. A.; Davis, G. A. J. Am. Chem. Soc. 1967, 89, 941-945.
45. (b) Barbara, G.; Battaglia, A.; Giorgianni, P. J. Org. Chem. 1995, 60, 1020-1025.
46. Bestmann, H. J. Angew. Chem. 1977, 89, 361-376.
47. (a) Marchand-Brynaert, J.; Ghosez, L. J. Am. Chem. Soc. 1972, 94, 2870-2872.
48. (b) Houge, C.; Frisque-Hesbain, A. M.; Mockel, A.; Ghosez, L.; Declercq, J. P.; Germain, G.; van Meerssche, M. J. Am. Chem. Soc. 1982, 104, 2920-2921.