Transitions of electron demand in pericyclic reactions: Normal, neutral, and inverse Diels-Alder reactions of polyhalogenated cyclopentadienes

Liebigs Annales

Volumn , Issue 12, 1997, Pages 2471-2484

  Eibler, Ernst ^a   Höcht, Peter ^a   Prantl, Bernhard ^a   Roßmaier, Henry ^a   Schuhbauer, Hans Markus ^a   Wiest, Hubert ^a   Sauer, Jürgen ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Cycloadditions; Neutral electron demand; Semiempirical calculations; Structure activity relationships; Substituent effects

Indexed keywords

EID: 33645479182     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719971209     Document Type: Article

References (85)

1. [1a] K. Alder, G. Stein, Angew. Chem. 1937, 50, 510-519.
2. [1b] J. G. Martin, R. K. Hill, Chem. Rev. 1961, 61, 537-562.
3. [1c] J. Sauer, Angew. Chem. 1966, 78, 233-252;
4. Angew. Chem. Int. Ed. Engl. 1966, 5, 211-230.
5. [1d] J. Sauer, Angew. Chem. 1967, 79, 76-93;
6. Angew. Chem. Int. Ed. Engl. 1967, 6, 16-33.
7. [1e] J. Sauer, R. Sustmann, Angew. Chem. 1980, 92, 773-801,
8. Angew. Chem. Int. Ed. Engl. 1980, 19, 779-807, and references cited therein.
9. [1f] D. L. Boger, S. M. Weinreb, Hetero-Diels-Alder-Methodology in Organic Synthesis (Organic Chemistry, vol. 47), Ed.: H. Wassermann, Academic Press Inc., San Diego 1987.
10. [1g] T. Kametami, S. Hibino in Advances in Heterocydic Chemistry, vol. 42 (Ed.: A. R. Katritzky), Academic Pres Inc., Orlando 1987, p. 245-333.
11. [1h] W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford 1990.
12. [1i] W. Oppolzer in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming and L. A. Paquette), Pergamon, Oxford 1991, p. 315-399.
13. S. M. Weinreb, Comprehensive Organic Synthesis (ibid., p. 401-449.
14. D. L. Boger, Comprehensive Organic Synthesis (ibid., 451-512.
15. W. R. Roush, Comprehensive Organic Synthesis (ibid., 513-550.
16. [1k] J. Sauer in Comprehensive Heterocyclic Chemistry II, Vol. 6 (Eds.: A. R. Katritzky, C. W. Rees and E. F. Scriven), Pergamon, New York 1996, p. 901-955.
17. For an enthralling review illuminating the "prehistory" of the discovery of the Diels-Alder reaction, see J. A. Berson, Tetrahedron (Perspectives) 1992, 48, 3-17, and references cited therein.
18. O. Diels, K. Alder, Liebigs Ann. Chem. 1928, 460, 98-122.
19. [4a] J. Sauer, H. Wiest, A. Mielert, Chem. Ber. 1964, 67, 3183-3207.
20. [1e]].
21. W. E. Bachmann, N. C. Deno, J. Am. Chem. Soc. 1949, 71, 3062.
22. R. A. Carboni, R. V. Lindsey Jr., J. Am. Chem. Soc. 1959, 81, 4342-4346.
23. J. Sauer, H. Wiest, Angew. Chem. 1962, 74, 353;
24. Angew. Chem. Int. Ed. Engl., 1962, 1, 269.
25. Early examples for neutral electron demand Diels-Alder reactions: [8a] A. I. Konovalov, Ya. D. Samuilov, L. F. Slepova, V. A. Breus, J. Org. Chem. USSR 1973, 9, 2539-2541.
26. [8b] A. I. Konovalov, B. N. Solomonov, O. Yu. Chertov, J. Org. Chem. USSR 1975, 11, 103-106,
27. A. I. Konovalov, B. N. Solomonov, O. Yu. Chertov, J. Org. Chem. USSR ibid, 107-109.
28. [8c] A. I. Konovalov, Ya. D. Samuilov, L. F. Uryadova, E. A. Berdnikov, J. Org. Chem. USSR 1976, 12, 636-639.
29. [8d] A. I. Konovalov, L. F. Uryadova, Ya. D. Samuilov, J. Org. Chem. USSR 1976, 12, 2519-2523.
30. [8e] M. Yasuda, K. Harano, K. Kanematsu, J. Org. Chem. 1980, 45, 659-664.
31. [1e] for an overview on neutral Diels-Alder reactions. A recent example involves 3-azanorcaradiene as the diene component: H. Stimmelmayer, Ph. D. Dissertation, Universität Regensburg 1992.
32. R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-869;
33. Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853.
34. The degree of concertedness and synchronicity in the mechanism of Diels-Alder reactions is a matter of ongoing scientific discussion, exceeding the scope of this treatise. For a recent review on pericyclic reaction transition states, see: K. N. Houk, J. Gonzalez and Y. Li, Acc. Chem. Res., 1995 28, 81-90, and references cited therein.
35. [11a] K. Fukui, Fortschr, Chem. Forsch. 1970, 15, 1-85.
36. [11b] K. Fukui, Acc. Chem. Res. 1971, 4, 57-64.
37. [12a] R. Sustmann, Tetrahedron Lett. 1971, 2717-2720;
38. R. Sustmann, Tetrahedron Lett. ibid, 2721-2724.
39. [12b] R. Sustmann, Pure Appl. Chem. 1974, 40, 569-593.
40. [12c] C. Rücker, D. Lang, J. Sauer, H. Friege, R. Sustmann, Chem. Ber. 1980, 113, 1663-1690.
41. [13a] K. N. Houk. J. Am. Chem. Soc. 1973, 95, 4092-4094.
42. [13b] K. N. Houk, J. Sims, C. R. Watts, L. J. Luskus, J. Am. Chem. Soc. 1973, 95, 7301-7315.
43. O. Exner in Correlation Analysis in Chemistry (Eds.: N. B. Chapman and J. Shorter), Plenum Press, New York 1978, p. 439-540.
44. [15a] H. C. Brown, Y. Okamoto, T. Inukai, J. Am. Chem. Soc. 1958, 80, 4964-4968.
45. [15b] Y. Okamoto, T. Inukai, H. C. Brown, J. Am. Chem. Soc. 1958, 80, 4969-4972,
46. Y. Okamoto, T. Inukai, H. C. Brown, J. Am. Chem. Soc. ibid. 4972-4976.
47. [15c] Y. Okamoto, H. C. Brown, J. Am. Chem. Soc. 1958, 80, 4976-4979.
48. [15d] Y. Okamoto, H. C. Brown, J. Am. Chem. Soc. 1958, 80, 4979-4987.
49. L. P. Hammett, J. Am. Chem. Soc. 1937, 59, 96-103.
50. [17a] H. Wiest, Ph. D. Dissertation, Universität München 1963.
51. [17b] B. Prantl, Ph. D. Dissertation, Universität Regensburg 1982.
52. [17c] H. Roßmaier, Diplomarbeit, Universität Regensburg 1983.
53. [17d] M. Raps, Ph. D. Dissertation, Universität Regensburg 1991.
54. [17e] P. Höcht, Ph. D. Dissertation, Universität Regensburg 1994.
55. [17f] H. Schuhbauer, Ph. D. Dissertation, Universität Regensburg 1995.
56. A. M. Mustafaev, M. M. Guseinov, Kh. I. Kasymov, J. Org. Chem. USSR 1986, 22, 1686-1690.
57. [19a] M. S. Salakhov, N. F. Musaeva, R. S. Salakhova, A. A. Aleskerov, S. N. Suleimanov, Org. React. (Tartu) 1977, 14, 295-300 [
58. Chem. Abstr. 1978, 89, 42131m].
59. [19b] M. S. Salakhov, N. F. Musaeva, R. S. Salakhova, S. N. Suleimanov, A. A. Aleskerov, Org. React. (Tartu) 1977, 14, 301-310
60. [Chem. Abstr. 1978, 89, 42132].
61. [19c] N. F. Musaeva, M. S. Salakhov, A. A. Aleskerov, S. N. Suleimanov, T. A. Kopylova, J. Org. Chem. USSR 1980, 16, 1181-1187, and references cited therein.
62. M. S. Salakhov, N. F. Musaeva, S. N. Suleimanov, A. A. Bairamov, J. Org. Chem. USSR 1979, 15, 2106-2112, and references cited therein.
63. M. E. Burrage, R. C. Cookson, S. S. Gupte, I. D. R. Stevens, J. Chem. Soc., Perkin Trans. 2 1975, 1325-1334.
64. A. M. Mustafaev, Kh. I. Kasymov, M. M. Guseinov, J. Org. Chem. USSR 1986, 22, 1281-1285.
65. N. F. Musaeva, M. S. Salakhov, V. S. Umaeva, J. Org. Chem. USSR 1981, 17, 105-109.
66. A. M. Mustafaev, M. R. Adigezalov, V. D. Kiselev, A. I. Konovalov, M. M. Guseinov, J. Org. Chem. USSR 1980, 16, 2179-2183.
67. A. M. Mustafaev, A. B. Imamaliev, M. M. Guseinov, J. Org. Chem. USSR 1987, 23, 1314-1317.
68. A. M. Mustafaev, A. B. Imamaliev, M. M. Guseinov, J. Org. Chem. USSR 1989, 25, 1724-1730.
69. E. Eibler, T. Burgemeister, P. Höcht, B. Prantl, H. Roßmaier, H. M. Schuhbauer, H. Wiest, J. Sauer, Liebigs Ann./Recueil, 1997, ((LA97186)), previous paper.
70. J. Sauer, H. M. Schuhbauer, Liebigs Ann./Recueil 1997, 1739-1743.
71. [29a] H. E. Simmons, T. Fukanaga, J. Am. Chem. Soc. 1967, 89, 5208-5215.
72. [29b] H. Dürr, R. Gleiter, Angew. Chem. 1978, 90, 591-601,
73. Angew. Chem. Int. Ed. Engl. 1978, 17, 559-569.
74. P. H. Daniels, Ph. D. Dissertation, University of Louisville 1979.
75. P. H. Daniels, J. L. Wong, J. Org. Chem. 1980, 45, 435-440.
76. In this paper, the authors corrected an initial incorrect assignment: C. M. Gladstone, P. H. Daniels, J. L. Wong, J. Org. Chem. 1977, 42, 1375-1379.
77. [27] for a detailed discussion on the structure elucidation of the heterodiene and its cycloadducts.
78. [32a] C. D. Ritchie, W. F. Sager, Prog. Phys. Org. Chem. 1964, 2, 323-400.
79. [32b] L. M. Stock, H. C. Brown, Adv. Phys. Org. Chem. 1963, 7, 35-154.
80. J. H. Espenson, Chemical Kinetics and Reaction Mechanisms, McGraw-Hill, New York 1981, p. 117-119.
81. PM3 semiempirical calculations on geometry-optimised and energy-minimised structures were carried out using Proquantum trade mark sign software (V 1.33, Oxford Molecular Ltd., Oxford OX4 46A) and Silicon Graphicstrade mark sign hardware.
82. L. C. Burry, J. N. Bridson, D. J. Burnell, J. Org. Chem. 1995, 60, 5931-5934.
83. [36a] S. Hünig, G. Märkl, J. Sauer, Integriertes Organisches Praktikum, VCH, Weinheim 1979.
84. [36b] Organikum, Autorenkollektiv, VEB Verlag der Wissenschaften, Berlin 1977.
85. [36c] D. D. Perrin, W. L. Armarego, D. R. Perrin, Purification of Laboratory Chemicals, 2nd ed., Pergamon Press, Oxford 1980.