Theoretical study of the Diels-Alder reaction between the S-methylthiophenium ion and ethene

Journal of the Chemical Society. Perkin Transactions 2

Volumn 3, Issue , 1996, Pages 455-459

  Jursic, Branko S ^a   Zdravkovski, Zoran ^a   Whittenburg, Scott L ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002115352     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29960000455     Document Type: Article

References (48)

1. D. Seebach, Angew. Chem., Int. Ed. Engl., 1990, 29, 1320;
2. B. Helmut, H.-D. Scharf, N. Hoffmann and F. Esser, Angew. Chem., Int. Ed. Engl., 1991, 30, 477;
3. E. J. Corey, Angew. Chem., Int. Ed. Engl., 1991, 30, 455;
4. L. F. Trietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131.
5. W. Carruther, Cycloaddition Reactions in Organic Synthesis, Pergamon, New York, 1990,
6. 1,4-Cycloaddition Reactions, ed. J. Hamer, Academic Press, New York, 1967;
7. M. E. Jung, K. Shishido, L. Light and L. Devis, Tetrahedron Lett., 1981, 4607;
8. F. Jensen and C. S. Foote, J. Am. Chem. Soc., 1987, 109, 6376;
9. B. Nader, T. R. Bailey, R. W. Franck and S. M. Weinreb, J. Am. Chem. Soc., 1981, 103, 7573;
10. L. Le Coz, C. Veyrat-Martin, L. Wartski, J. Seyden-Penne, C. Bois and M. Philoche-Levisalles, J. Org. Chem., 1990, 55, 4870;
11. S. J. Danishefsky, E. Larson, D. Askin and N. Kato, J. Am. Chem. Soc., 1985, 107, 1246;
12. S. J. Danishefsky, H. G. Selznik, R. E. Zelle and M. P. Deninno, J. Am. Chem. Soc., 1988, 110, 4368;
13. S. J. Danishefsky, D. C. Myles and D. F. Harrey, J. Am. Chem. Soc., 1987, 109, 862;
14. M. Bednarsky and S. J. Danishefsky, J. Am. Chem. Soc., 1986, 108, 7060;
15. K. F. McCule, J. W. Benbow and S. J. Danishefsky, J. Am. Chem. Soc., 1991, 113, 8185.
16. For some reviews, see: A. Wasserman, Diels-Alder Reactions, Elsevier, New York, 1965;
17. W. R. Roush, Adv. Cycloaddition, 1990, 2, 91;
18. G. Brieger and J. N. Bennett, Chem. Rev., 1980, 80, 63.
19. B. S. Jursic, Z. Zdravkovski and S. L. Whittenburg, J. Phys. Org. Chem., 1995, 8, 753.
20. For review of aromaticity and structural characteristics of five-membered aromatic rings with one heteroatom, see: C. W. Bird and G. W. H. Cheeseman, Comprehensive Heterocyclic Chemistry, eds. A. Katritzky and C. H. Rees, Pergamon Press, New York, 1984.
21. B. S. Jursic and D. Coupe, J. Heterocycl. Chem., 1995, 32, 483.
22. Recently we have performed a theoretical study of different reactivities of benzothiophenes, based on their different aromaticity. The same approach can be used for comparison of the reactivity of thiophene and the thiophenium ion. B. S. Jursic, J. Heterocycl. Chem., in the press.
23. GAUSSIAN92/DFT, Revision G.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. W. Wong, J. B. Foresman, M. A. Robb, M. Head-Gordon, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart and J. A. Pople, Gaussian Inc., Pittsburgh PA, 1993.
24. M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman and C. C. J. Roothaan, Rev. Mod. Phys., 1951, 23, 69.
25. R. Gomperts, J. L. Andres, K. Raghavachari and J. S. Binkley, 1980, 102, 939; M. S. Gordon, J. S. Binkley, J. C. Pople, R. L. Gonzalez, D. J. Martin, D. J. Fox, J. Defrees, J. Baker and W. J. Hehre, J. Am. Chem. Soc., 1982, 104, 2797.
26. M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees and J. A. Pople, J. Chem. Phys., 1982, 77, 3654.
27. P. Carsky, B. A. Hess and L. J. Schaad, J. Comput. Chem., 1984, 5, 280.
28. M. J. S. Dewar, S. Olivella and J. J. P. Stewart, J. Am. Chem. Soc., 1986, 108, 5771;
29. M. J. S. Dewar, Profile, Pathways and Dreams, ed. X. Seeman, 1992, pp. 150-152;
30. M. J. S. Dewar and C. Jie, Acc. Chem. Res., 1992, 25, 537 and references therein.
31. Y. Li and K. N. Houk, J. Am. Chem. Soc., 1993, 115, 7478 and references therein.
32. All calculations were carried out with MOPAC version 6.0. Quantum Chemistry Program Exchange (QCPE), Program Number 455, 1990; M. J. S. Dewar, E. G. Zoebish, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
33. B. Back, D. Christensen, L. Hansen-Nygaard and J. Rastrup-Andersen, J. Mol. Spectrosc., 1961, 7, 58.
34. J. A. Hashmall, V. Horak, L. E. Khoo, C. O. Quickall and M. K. Sun, J. Am. Chem. Soc., 1981, 103, 289.
35. R. J. Gillespie, J. Murray-Rust, P. Murray-Rust and A. E. Porter, J. Chem. Soc., Chem. Commun., 1978, 83.
36. R. F. Heldeweg and H. Hogeveen, Tetrahedron Lett., 1974, 75.
37. K. Fukui and H. Fujimoto, Bull. Chem. Soc. Jpn., 1967, 40, 2018;
38. K. Fukui and H. Fujimoto, Bull. Chem. Soc. Jpn., 1969, 42, 2018;
39. K. Fukui, Angew. Chem., Int. Ed. Engl., 1982, 21, 801.
40. K. N. Houk, in Pericyclic Reactions, eds. A. P. Marchand and R. E. Lehr, Academic Press, New York, 1977, vol. II, p. 203;
41. K. N. Houk, Top. Curr. Chem., 1979, 79, 33.
42. F. Bernardi, A. Bottoni, M. J. Field, M. F. Guest, I. H. Hillier, M. A. Robb and A. Venturini, J. Am. Chem. Soc., 1988, 110, 3050;
43. R. D. Bach, J. W. Mc.Douall and H. B. Schlegel, J. Org. Chem., 1989, 54, 2931 and references therein.
44. D. Rowley and H. Steiner, Discuss. Faraday Soc., 1951, 10, 198.
45. B. S. Jursic and Z. Zdravkovski, J. Mol. Struct. (Theochem), 1995, 343, 149.
46. K. Houk, Y.-T. Lin and J. D. Evanseck, Angew. Chem., Int. Ed. Engl., 1992, 31, 682.
47. B. S. Jursic and Z. Zdravkovski, J. Chem. Soc., Perkin Trans. 2, 1995, 1223.
48. B. S. Jursic and Z. Zdravkovski, J. Comp. Chem., in the press.