Thio- and Selenocarbonyl Compounds as "Superdienophiles" in [4+2] Cycloadditions

European Journal of Organic Chemistry

Volumn , Issue 12, 1998, Pages 2875-2883

  Rohr, Uwe ^a   Schatz, Jürgen ^a,b   Sauer, Jürgen ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF ULM   (Germany)

Author keywords

Cycloadditions; Selenocarbonyl compounds; Solvent effects; Substitution effects; Thiocarbonyl compounds

Indexed keywords

EID: 0003128026     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199812)1998:12<2875::aid-ejoc2875>3.0.co;2-n     Document Type: Article

References (67)

1. O. Diels, K. Alder, Justus Liebigs Ann. Chem 1928, 460, 98-122.
2. J. Sauer, R. Sustmann, Angew. Chem. 1980, 92, 773-801; Angew. Chem. Int. Ed. Engl. 1980, 19, 779-807.
3. J. Sauer, R. Sustmann, Angew. Chem. 1980, 92, 773-801; Angew. Chem. Int. Ed. Engl. 1980, 19, 779-807.
4. J. Hamer 1.4-Cycloaddition Reactions, Academic Academic Press, New York, 1967.
5. D. L. Boger, N. Weinreb in Hetero-Diels-Alder Methodology (Ed.: H. Wassermann), Academic Press, New York, 1987, vol. 47.
6. J. Sauer, H. Wiest, A. Mielert, Chem. Ber. 1964, 67, 3183-3207.
7. J. Sauer, D. Lang, H. Wiest, Chem. Ber. 1964, 67, 3208-3218.
8. W. E. Bachmann, N. C. Deno, J. Am. Chem. Soc. 1949, 71, 3062-3072.
9. R. A. Carboni, R. V. J. Lindsey, J. Am. Chem. Soc. 1959, 81, 4342-4346.
10. J. Sauer, H. Wiest, Angew. Chem. 1962, 74, 353; Angew. Chem. Int. Ed. Engl. 1962, 1. 269.
11. J. Sauer, H. Wiest, Angew. Chem. 1962, 74, 353; Angew. Chem. Int. Ed. Engl. 1962, 1. 269.
12. R. B. Woodward, R. Hoffmann, Angew. Chem 1969, 81, 797-869; Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853.
13. R. B. Woodward, R. Hoffmann, Angew. Chem 1969, 81, 797-869; Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853.
14. R. Sustmann, Pure Appl Chem. 1974, 40, 569-593.
15. K. Fukui, Acc. Chem. Res. 1971, 4, 57-64.
16. K. N. Houk, J. Am. Chem. Soc 1973, 95, 4092-4094.
17. K. N. Houk, J. Sims, C. R. Watts, L. J. Luskus, J. Am. Chem. Soc. 1973, 95, 7301-7315.
18. O Exner in Correlation Analysis in Chemistry (Eds. N. B. Chapman, J. Shorter), Plenum Press, New York, 1978, p. 439.
19. H. C. Brown, Y. Okamoto, T. Inukai, J. Am. Chem. Soc. 1958, 80, 4964-4968.
20. L. P Hammett, J Am Chem. Soc. 1937, 59, 69-103.
21. C. Reichardt, Solvent and Solvent Effects in Organic Chemistry, 2nd ed., VCH, Weinheim, 1988, p. 121ff.
22. D. C. Rideout, R. Breslow, J Am. Chem. Soc. 1980, 102, 1816-7817.
23. A. Lubineau, J. Org. Chem. 1986, 51, 2142-2144.
24. P. A. Grieco, Aldrichim. Acta 1991, 24, 59-66.
25. J. B. F. N. Engberts, Pure Appl. Chem. 1995, 67, 823-828.
26. J. W. Wijnen, J. B. F. N. Engberts, Liebigs Ann. 1997, 1085-1088.
27. J. Sauer, F. Schuster, R. Braun, Tetrahedron Lett. 1986, 27, 1285-1288.
28. C. J. Li, T. H. Chan, Organic Reactions in Aqueous Media, John Wiley and Sons, New York, 1997.
29. Organic Synthesis in Water (Ed.: P. A. Grieco), Blackie Academic and Professional, London, 1998.
30. K. Dimroth, C. Reichardt, T. Siepmann, F. Bohlmann, Justus Liebigs Ann. Chem 1963, 661, 1-37.
31. V. Gutmann, E. Wychera, Inorg. NUcl. Chem. Lett. 1966, 2, 257-260.
32. V. Gutmann, U. Mayer, W. Gerger, Monatsh. Chem. 1975, 106, 1235-1257.
33. E. M. Kosower, J. Am. Chem. Soc. 1958, 80, 3253-3260.
34. J. Hormadaly, Y. Marcus, J Phys. Chem 1960, 38, 1590-1596.
35. S. Brownstein, Can. J. Chem. 1960, 38, 1590-1596.
36. J. A Berson, Z. Hamlet, W. A. Mueller, J. Am Chem. Soc 1962, 84, 297-304.
37. T. Oshima, S. Arikata, T. Nagai, J. Chem. Res (S) 1981, 204-205.
38. S. Winstein, S. G. Smith, A. H. Fainbcrg, J. Am. Chem Soc. 1961, 83, 618-625.
39. C. G. Swain, M. S. Swain, A. L. Powell, S. Alunm, J. Am. Chem. Soc. 1983, 105, 502-513.
40. J. Catalan, C. Diaz, V. Lopez, P. Perez, J.-L. G. de Paz, J. G. Rodriguez, Liebigs Ann. 1996, 1785-1794.
41. I. A. Koppel, V. A. Palm in Advances in Linear Free-Energy Relationships (Eds: N. B. Chapmann, J. Shorter), Plenum, London, 1972, p. 203.
42. M. J. Kamlet, M. E. Jones, R. W. Taft, J Chem. Soc., Perkin Trans. 2 1979, 349-356.
43. R. Huisgen, L. Fisera, H. Giera, R. Sustmann, J. Am. Chem. Soc. 1995, 117, 9671-9678.
44. R. Huisgen, H. Giera, Liebigs Ann. 1997, 1685-1689.
45. R. Huisgen, X. Li, Tetrahedron Lett. 1983, 24, 4185-4188.
46. R. Huisgen, E. Langhals, Tetrahedron Lett. 1989, 30, 5369-5372.
47. J. Schatz, J. Sauer, Tetrahedron Lett. 1994, 35, 4767-4770.
48. J. Breu, P. Höcht, U. Rohr, J. Schatz, J. Sauer, Eur. J. Org. Chem. 1998, 2861-2873.
49. J. Drexler, M. A. Lmdermayer, M. A. Hassan, J. Sauer, Tetrahedron Lett. 1985, 26, 2559-2562.
50. C. Rücker, D. Lang, J. Sauer, H. Friege, R. Sustmann, Chem. Ber. 1980, 113, 1663-1690.
51. R. Sustmann, private communication.
52. J. Drexler, Ph. D. Dissertation. University of Regensburg, 1984.
53. H. Adam, Ph. D. Dissertation, University of Regensburg, 1994.
54. E. Eibler, T. Burgemeister, P. Höcht, B. Prantl, H. Roßmaier, H. Schuhbauer, H. Wiest, J. Sauer, Liebigs Ann. 1997, 2451-2469.
55. E. Eibler, P. Höcht, B. Prantl, H. Roßmaier, H. Schuhbauer, H. Wiest. J. Sauer, Liebigs Ann. 1997, 2471-2484.
56. P. Höcht, Ph. D. Dissertation, University of Regensburg, 1994.
57. J. Hamer, M. Ahmad, J. Org. Chem. 1966, 31, 2829-2833.
58. J. Sauer, Bull. Soc. Chim. Belg. 1992, 101, 521-540.
59. J. Sauer in 1,2,4,5-Tetrazines (Eds.: Ch. W. Rees, A J. Boulton, A. R. Katritzky), Pergamon Press, Oxford, 1996, vol. 6, p. 901.
60. I. El-Sayed, M. F. Abdel-Megeed, S. Yassin, A. Senning, Sulfur Lett. 1992, 15, 1-4.
61. H. Eyring, Chem. Rev 1935, 17, 65-79.
62. A. Battaglia, A. Dondoni, G. Maccagnani, G. Mazzant, J. Chem. Soc. B 1971, 2096-2100.
63. J. Schatz, Ph. D. Dissertation, University of Regensburg, 1994.
64. U. Rohr, Ph. D Dissertation, University of Regensburg, 1996.
65. G. Erker, F.-G. Klärner, R. Hock, C. Krüger, S. Werner, U. Artschwanger-Perl, Angew Chem. 1990, 102, 1082-1084; Angew. Chem. Int. Ed. Engl. 1990, 29. 1067-1069.
66. G. Erker, F.-G. Klärner, R. Hock, C. Krüger, S. Werner, U. Artschwanger-Perl, Angew Chem. 1990, 102, 1082-1084; Angew. Chem. Int. Ed. Engl. 1990, 29. 1067-1069.
67. R. Huisgen, Pure Appl. Chem. 1989, 61, 613-628.