Theoretical studies on the gas-phase nucleophilic ring opening of 3,4-epimino-, 3,4-epoxy-, and 3,4-epithio-1-butene

Journal of Physical Chemistry A

Volumn 101, Issue 15, 1997, Pages 2893-2899

  Lee, Jin Kak ^a   Kim, Chang Kon ^a   Lee, Bon Su ^a   Lee, Ikchoon ^a  

^a Inha University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001712507     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9632697     Document Type: Article

References (52)

1. (a) Bartok, M.; Lang, K. L. The Chemistry of Functional Groups. Supplement E. The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and Their Sulfur Analogues, Part 2; Patai, S., Ed.; Wiley, New York, 1980; pp 609-682.
2. (b) Lewors, E. G. Comprehensive Heterocyclic Chemistry, Part 5 (Small and Large Rings); Lwowaki, W., Ed.; Pergamon; New York, 1984; pp 95-130.
3. (a) Freedman, R. W.; Becker, E. I. J. Org. Chem. 1951, 16, 1701.
4. (b) Rose, C. B.; Smith, C. W., Jr. Chem. Commun. 1969, 248.
5. (c) Herr, R. W.; Johnson, C. R. J. Am. Chem. Soc. 1970, 92, 4979.
6. Anderson, R. J. J. Am. Chem. Soc. 1970, 92, 4978.
7. Benson, S. W. Thermochemical Kinetics; Wiley: New York, 1968; See Appendix, Tables A1-A5.
8. Klumpp, G. W. Reactivity in Organic Chemistry; Wiley: New York, 1982; p 38.
9. Stirling, C. J. M. Tetrahedron 1985, 41, 1613.
10. (a) Apparu, M.; Barrelle, M. Tetrahedron 1978, 34, 1691, 1817.
11. (b) Cape, A. C.; Heeren, J. K. J. Am. Chem. Soc. 1965, 87, 3125.
12. (c) Thummel, R. P.; Rickborn, B. J. Am. Chem. Soc. 1970, 92, 2064.
13. (d) Thummel, R. P.; Rickborn, B. J. Org. Chem. 1972, 37, 3919.
14. Piras, P. P.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 2 1987, 1265.
15. Bordwell, F. G.; Anderson, H. M.; Pitt, B. M. J. Am. Chem. Soc. 1954, 74, 1082.
16. (a) Riveros, J. M.; Jose, S. M.; Takashima, I. Adv. Phys. Org. Chem. 1985, 21, 197.
17. (b) Pellerite, M. J.; Brauman, J. I. J. Am. Chem. Soc. 1983, 105, 2672.
18. (c) Wladkowaski, B. D.; Wilbur, J. L.; Brauman, J. I. J. Am. Chem. Soc. 1994, 116, 2471.
19. (d) O'Hair, R. A. J.; Davico, G. E.; Hacaloglu, J.; Dang, T. T.; De Puy, C. H.; Bierbaum, V. M. J. Am. Chem. Soc. 1994, 116, 3609.
20. (a) Asubiojo, O. I.; Brauman, J. I. J. Am. Chem. Soc. 1979, 101, 3715.
21. (b) Han, C.-C.; Brauman, J. I. J. Am. Chem. Soc. 1987, 109, 589.
22. (c) Han. C.-C.; Brauman, J. I. J. Am. Chem. Soc. 1990, 112, 7835.
23. (d) Wilbur, J. L; Brauman, J. I. J. Am. Chem. Soc. 1994, 116, 5839.
24. Bierbaum, V. M.; De Puy, C. H.; Shapiro, R. H.; Stewart, J. H. J. Am. Chem. Soc. 1976, 98, 4229.
25. De Puy, C. H.; Beedle, E. C.; Bierbaum, V. M. J. Am. Chem. Soc. 1982, 104, 6483.
26. Groner, S.; Lee, J. M. J. Org. Chem. 1995, 60, 4488.
27. Cremer, D.; Kraka, E. J. Am. Chem. Soc. 1985, 107, 3800.
28. Ford, G. P.; Smith, C. T. J. Am. Chem. Soc. 1987, 109, 1325.
29. Glad, S. S.; Jensen, F. J. Chem. Soc., Perkin Trans. 2 1994, 871.
30. Gronert, S. J. Am. Chem. Soc. 1991, 113, 6041.
31. (a) De Puy, C. H.; Gronert, S.; Mullin, A.; Bierbaum, V. M. J. Am. Chem. Soc. 1990, 112, 8650.
32. (b) Gronert, S.; De Puy, C. H.; Bierbaum, V. M. J. Am. Chem. Soc. 1991, 113, 4009.
33. (c) Lum, R. C.; Grabowski. J. J. J. Am. Chem. Soc. 1992, 114, 9663.
34. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A.; Gaussian 92 Gaussian, Inc.: Pittsburgh, PA, 1992.
35. (a) Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
36. (b) Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229.
37. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Willey: New York, 1986; pp 251-260.
38. Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 119.
39. N2 Mechanism; Wiley: New York, 1992; pp 253-256.
40. (b) Lee, I.; Kim, C. K.; Lee, B-S. J. Comput. Chem. 1995, 16, 1045.
41. Pauling, L. J. Am. Chem. Soc. 1947, 69, 542.
42. (b) Johnston, H. S. Gas Phase Reaction Rate Theory; Ronald Press: New York, 1996; pp 80-83.
43. Jencks, W. P. Chem. Rev. 1972, 72, 705.
44. (b) Paolini, J. P. J. Comput. Chem. 1990, 11, 1160.
45. (c) Rodgers, J.; Femec, D. A.; Schomen, R. L. J. Am. Chem. Soc. 1982, 104, 3263.
46. Houk, K. N.; Gustafson, S. M.; Black, K. A. J. Am. Chem. Soc. 1992, 114, 8565.
47. Dewar, M. J. S. The Molecular Orbital Theory of Organic Chemistry; McGraw-Hill: New York, 1969; p 284.
48. (b) Reference 5, p 328.
49. (a) Leffler, J. E. Science 1953, 117, 340.
50. (b) Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
51. (c) Reference 5, p 326.
52. Lee, I.; Kim, C. K.; Chung, D. S.; Lee, B.-S. J. Org. Chem. 1994, 59, 4490.