A computational study of aromaticity-controlled Diels-Alder reactions

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 8, 2000, Pages 1767-1773

  Manoharan, Mariappan ^a   De Proft, Frank ^a   Geerlings, Paul ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; AROMATIZATION; BUTADIENE; COMPUTATIONAL METHODS; ETHYLENE; MAGNETIC SUSCEPTIBILITY; PHASE TRANSITIONS; REACTION KINETICS; THERMODYNAMIC PROPERTIES;

CYCLOADDITIONS; DIELS-ALDER REACTIONS; MAGNETIC SUSCEPTIBILITY EXALTATION; NUCLEUS INDEPENDENT CHEMICAL SHIFT;

ADDITION REACTIONS;

EID: 0034256638     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002344m     Document Type: Article

References (132)

1. (a) A. P. Marchand and R. E. Lehr, Pericyclic Reactions, Academic Press, New York, 1977
2. (b) W. Carruthers, Cycloaddition Reactions in Organic Synthesis; Tetrahedron Organic Chemistry Series, Pergamon, Elmsford, NY, 1990
3. (c) L. Boger and S. N. Weinberg, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, New York, 1987
4. (d) J. Sauer, Angew, Chem., Int. Ed. Engl., 1967, 6, 16
5. (e) R. Huigen, Acc. Chem. Res., 1977, 10, 199
6. (f) J. Sauer and R. Sustmann, Angew. Chem., Int. Ed. Engl., 1980, 18, 779
7. (g) N. L. Bauld, Tetrahedron, 1989, 45, 5307
8. (h) J. A. Berson, Tetrahedron, 1992, 48, 3
9. (i) J. D. Winkler, Chem. Rev., 1996, 95, 167.
10. (a) R. B. Woodward and R. Hoffmann, Angew. Chem., Int. Ed. Engl., 1969, 8, 781
11. (b) R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Weinheim, 1970
12. (c) I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, Chichester, 1976, pp. 137-166.
13. (a) W. T. Borden, R. J. Loncharich and K. N. Houk, Annu. Rev. Phys. Chem., 1988, 39, 213
14. (b) F. Bernardi, M. Olivucci and M. A. Robb, Acc. Chem. Res., 1990, 23, 405
15. (c) M.J.S. Dewar, Acc. Chem. Res., 1992, 25, 537
16. (d) K. N. Houk, Y. Li and J. D. Evanseck, Angew. Chem., Int. Ed. Engl., 1992, 31, 682
17. (e) J. E. Eksterowicz and K. N. Houk, Chem. Rev., 1993, 93, 2439
18. (f) K. N. Houk, J. Gonzalez and Y. Li, Acc. Chem. Res., 1995, 28, 81
19. (g) O. Wiest and K. N. Houk, Top. Curr. Chem., 1996, 183, 1.
20. (a) B. A. Horn, J. L. Herek and A. H. Zewail, J. Am. Chem. Soc., 1996, 118, 8755
21. (b) M. Rouhi, Chem. Eng. News, 1996, 34
22. (c) S. Wilsey, K. N. Houk and A. H. Zewail, J. Am. Chem. Soc., 1999, 121, 5772.
23. (a) I. Klundt, Chem. Rev., 1980, 70, 471
24. (b) S. H. Quinkert, Angew. Chem., Int. Ed. Engl., 1983, 22, 637
25. (c) H. N. C. Wong, K.-L. Lau and K.-K. Tam, Top. Curr. Chem., 1986, 133, 85
26. (d) J. L. Charlton and M.M. Alauddin, Tetrahedron, 1987, 43, 2873
27. (e) M. Martin, C. Seoane and M. Hanack, Org. Prep. Proced. Int., 1991, 23, 237
28. (f) J. L. Segura and N. Martin, Chem. Rev., 1999, 99, 3199.
29. (a) S.V. D'Andrea, J.P. Freeman and J. Szmuskovicz, J. Org. Chem., 1990, 55, 4356
30. (b) Y. Rubin, S. Khan, D. I. Freedberg and C. Yeretzain, J. Am. Chem. Soc., 1993, 115, 344
31. (c) J. P. Parakka, E. V. Sadanandan and M. P. Cava, J. Org. Chem., 1994, 59, 4308
32. (d) P. Nelik, A. Gügel, M. Walter and K. Müllen, J. Org. Chem., 1995, 60, 3307
33. (e) T. A. Kshirsagar and P. S. Portoghese, J. Org. Chem., 1998, 63, 1706
34. (f) K. N. Laali, S. Hollenstein, S. E. Galembeck, Y. Nakamura and J. Nishimura, J. Chem. Soc., Perkin Trans. 2, 1999, 2129.
35. (a) U. Pindur and H. Erfanian-Abdoust, Chem. Rev., 1989, 89, 1681
36. (b) M. Haber and U. Pindur, Tetrahedron, 1991, 47, 1925
37. (c) A. Tomé, J. A. S. Cavaleiro and R. C. Storr, Tetrahedron Lett., 1993, 34, 6639
38. (d) T. Chou, Rev. Heteroat. Chem., 1993, 8, 65
39. (e) T. Chou and C. Ko, Tetrahedron, 1994, 50, 10721
40. (f) P. R. Carly, S. L. Cappelle, F. Compernolle, G. J. Hoornaert. Tetrahedron, 1996, 52, 11889
41. (g) G. Torres-Garcia, H. Luftmann, C. Wolff and J. Mattay, J. Org. Chem., 1997, 62, 2752
42. (h) U. M. Fernández, B. Illescas, N. Martin, C. Seoane, P. Cruz, A. Hoz and F.J. Langa, J. Org. Chem., 1997, 62, 3705
43. (i) B. González, A. Herrera, B. Illescas, N. Martin, R. Martinez, F. Moreno, L. Sánchez and A. Sánchez, J. Org. Chem., 1998, 63, 6807
44. (j) N. Martin, A. Martínez-Grau, C. Seoane and M. Torres, J. Org. Chem., 1998, 63, 8074.
45. (a) S. E. Whitney, M. Winters and B. Rickborn, J. Org. Chem., 1990, 55, 929
46. (b) K. R. Buszek, Tetrahedron Lett., 1995, 36, 9125
47. (c) R. Warmuth, Chem. Commun., 1998, 59
48. (d) T. Kitamura, N. Fukatsu and Y. Fujiwara, J. Org. Chem., 1998, 63, 8579.
49. (a) W. E. Bachmann and L. B. Scott, J. Am. Chem. Soc., 1948, 70, 1458
50. (b) D. E. Van Sickle and J. O. Rodin, J. Am. Chem. Soc., 1964, 86, 3091
51. (c) M. Taagepera and E. R. Thornton, J. Am. Chem. Soc., 1972, 94, 1168
52. (d) Y. Chung, B. F. Duerr and T. A. McKelvey, J. Org. Chem., 1989, 54, 1018
53. (e) M. Kar, T. G. Lenz and J. D. Vaughan, J. Chem. Thermodyn., 1992, 24, 151
54. (f) S. Fukuzumi and T. Okamoto, J. Am. Chem. Soc., 1993, 115, 11600
55. (g) M. Tsuda, T. Ishida, and S. Kuronon, J. Chem. Soc., Chem. Commun., 1993, 1296
56. (h) K. Komatsu, Y. Murata and N. Sugita, Tetrahedron Lett., 1993, 34, 8473
57. (i) F. A. McCormick and D. Marqurdt, Tetrahedron Lett., 1994, 35, 5169
58. (j) K. Mikami, S. Matsumoto, T. Tonoi and Y. Okubo, Tetrahedron Lett., 1998, 39, 3733
59. V.D. Kiselev, E.A. Kashaeva and A.I. Konovalov, Tetrahedron, 1999, 55, 1153.
60. (a) K. Liou, T. Hsiao and C. Cheng, Fullerene Sci. Technol., 1998, 8, 331
61. (b) Y. Murata, N. Kato, K. Fujiwara and K. Komatsu, J. Org. Chem., 1999, 64, 3483.
62. (a) M. Lora-Tamayo, Tetrahedron, 1958, 4, 17
63. (b) W. E. Bachmann and L. B. Scott, J. Am. Chem. Soc., 1948, 70, 1462
64. (c) W. E. Bachmann and N. C. Deno, J. Am. Chem. Soc., 1949, 71, 3062
65. (d) M. C. Carreño, R. Hernández-Sánchez, J. Mahugo and A. Urbano, J. Org. Chem., 1999, 64, 1387.
66. (a) B. Kräulter and J. Maynollo, Angew. Chem., Int. Ed. Engl., 1995, 34, 87
67. (b) F. Diederich and C. Thilgen, Science, 1996, 271, 317
68. (c) C. Thilgen, A. Herrmann and F. Diederich, Angew. Chem., Int. Ed. Engl., 1997, 36, 2268.
69. (a) J. Gonzalez, E.C. Taylor and K.N. Houk, J. Org. Chem., 1992, 57, 3753
70. (b) B. S. Jursic and Z. Zdravkovski, J. Chem. Soc., Perkin Trans. 2, 1994, 1877
71. (c) B. S. Jursic and Z. Zdravkovski, J. Org. Chem., 1994, 59, 3015
72. (d) B. S. Jursic and Z. Zdravkovski, J. Org. Chem., 1995, 60, 2865
73. (e) B. S. Jursic, J. Org. Chem., 1995, 60, 4721
74. (f) B. S. Jursic, J. Heterocycl. Chem., 1998, 35, 1467
75. (g) B. S. Jursic, J. Chem. Soc., Perkin Trans. 2, 1999, 373.
76. (a) J. W. Storer, L. Raimondi and K. N. Houk, J. Am. Chem. Soc., 1994, 116, 9675
77. (b) B. S. Jursic, J. Chem. Soc., Perkin Trans. 2, 1995, 1217
78. (c) B. S. Jursic, Can. J. Chem., 1996, 74, 114
79. (d) M. Solà, M. Duran and J. Mestres, J. Am. Chem. Soc., 1996, 118, 8920
80. (e) B. S. Jursic, Tetrahedron, 1997, 53, 13285
81. (f) I. Chao, H. Lu and T. Chou, J. Org. Chem., 1997, 62, 7882
82. (g) M. Manoharan and P. Venuvanalingam, J. Phys. Org. Chem., 1998, 11, 133
83. (h) J. Mestres and M. Solà, J. Org. Chem., 1998, 63, 7556
84. (i) K. E. Wise and R. A. Wheeler, J. Phys. Chem. A, 1999, 103, 8279.
85. (a) V. I. Minkin, M. N. Glukhovtsev and B. Y. Simkin, in Aromaticity and Antiaromaticity - Electronic and Structural Aspects, John Wiley and Sons, New York, 1994
86. (b) A. R. Katritzky, P. Barczynski, G. Masumarra, D. Pisano and M. Szafran, J. Am. Chem. Soc., 1989, 111, 7
87. (c) C. W. Bird, Tetrahedron, 1996, 29, 9945
88. (d) P.v.R. Schleyer and H. Jiao, Pure Appl. Chem., 1996, 68, 209.
89. A. Puplovskis, J. Kacens and O. Neilands, Tetrahedron Lett., 1997, 38, 285.
90. (a) A. R. Katritzky, Handbook of Heterocyclic Chemistry, Pergamon Press, New York, 1985
91. (b) L. F. Fieser and M. J. Haddadin, J. Am. Chem. Soc., 1964, 86, 2081
92. (c) L. F. Fieser and M. J. Haddadin, Can. J. Chem., 1965, 43, 1599
93. (d) W. Friedrichsen, Adv. Heterocycl. Chem., 1980, 26, 135
94. (e) R. Rodrigo, Tetrahedron, 1988, 44, 2093
95. (f) S. E. Whitney, M. Winters and B. Rickborn, J. Org. Chem., 1990, 55, 929.
96. (a) R. Mayer, S. Richter and K. Gewald, J. Prakt. Chem., 1963, 20, 244
97. (b) B. Iddon, Adv. Heterocycl. Chem., 1972, 14, 331.
98. M. Manoharan, F. De Proft and P. Geerlings, J. Org. Chem., submitted for publication.
99. (a) M. G. Evans and E. Warhurst, Trans. Faraday Soc., 1938, 34, 614
100. (b) H. Zimmerman, Acc. Chem. Res., 1971, 33, 272.
101. (a) R. Herges, H. Jiao and P.v.R. Schleyer, Angew. Chem., Int. Ed. Engl., 1994, 33, 1376
102. H. Jiao and P.v.R. Schleyer, J. Chem. Soc., Perkin Trans. 2, 1994, 407;
103. H. Jiao and P.v.R. Schleyer, Angew. Chem., Int. Ed. Engl., 1995, 34, 334
104. (d) F. Bernadi, P. Celani, M. Olivucci, M.A. Robb, and G. Suzzi-Valli, J. Am. Chem. Soc., 1995, 117, 10531
105. (e) H. Jiao and P. v. R. Schleyer, J. Am. Chem. Soc., 1995, 117, 11529
106. (f) I. Morao, B. Lecea and F. P. Cossio, J. Org. Chem., 1997, 62, 7033
107. (g) H. Jiao and P. v. R. Schleyer, J. Phys. Org. Chem., 1998, 11, 655
108. (h) I. Marao and F. P. Cossio, J. Org. Chem., 1999, 64, 1868
109. (i) F. P. Cossio, I. Maroa, H. Jiao and P.v.R. Schleyer, J. Am. Chem. Soc., 1999, 121, 6737
110. (j) D. Sawicka, S. Wilsey and K.N. Houk, J. Am. Chem. Soc., 1999, 121, 864
111. (k) D. Sawicka, Y. Li and K. N. Houk, J. Chem. Soc., Perkin Trans. 2, 1999, 2349.
112. J. H. Dauben, J. D. Wilson, Jr. and J. I. I. Laity, J. Am. Chem. Soc., 1968, 90, 1390.
113. P.v.R. Schleyer, C. Maerker, K. Dransfield, H. Jiao and J.R. van Eikema Hommes, J. Am. Chem. Soc., 1996, 118, 6317.
114. W. J. Hehre, L. Radom, P. v. R. Schleyer and J. Pople, Ab initio Molecular Orbital Theory, John Wiley & Sons, New York, 1986.
115. M. J. Frisch, G. H. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, GAUSSIAN 94, Revision B.3, Gaussian, Inc., Pittsburgh, PA, 1995.
116. (a) A. D. Becke, J. Chem. Phys., 1993, 98, 5648
117. (b) A. D. Becke, Phys. Rev. A, 1998, 38, 3098
118. (c) C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1980, 37, 785.
119. L. T. Nguyen, T. N. Le, F. De Proft, A. K. Chandra, W. Langenaeker, M. T. Nguyen and P. Geerlings, J. Am. Chem. Soc., 1999, 121, 5992
120. T. N. Le, L. T. Nguyen, F. De Proft, A. K. Chandra, P. Geerlings and M. T. Nguyen, J. Chem. Soc., Perkin Trans. 2, 1999, 1249.
121. K. Choho, G. Van Lier, G. Van de Woude and P. Geerlings, J. Chem. Soc., Perkin Trans. 2, 1996, 1723.
122. P. Geerlings, F. De Proft and W. Langenaeker, Density Functional Methods: Applications in Chemistry and Materials Science, M. Springborg, Ed., John Wiley, New York, 1997, ch. 2.
123. P. Geerlings, F. De Proft and W. Langenaeker, Adv. Quantum Chem., 1999, 33, 303.
124. P. Geerlings and F. De Proft, Chem. Rev., in preparation.
125. J. R. Cheeseman, G. W. Truck, T. A. Keith and J. Frisch, J. Chem. Phys., 1996, 104, 5497.
126. K. Wolinski, J. F. Hilton and P. Pulay, J. Am. Chem. Soc., 1990, 112, 8251
127. T. A. Keith and R. F. W. Bader, Chem. Phys. Lett., 1993, 210, 223.
128. The weakness of formed bonds and the tightness of cleaved bonds generally lead to bond make-break process at the TS to be fast.
129. G. S. Hammond, J. Am. Chem. Soc., 1955, 77, 3.
130. G. Subramanian, P. v. R. Schleyer and H. Jiao, Angew. Chem., Int. Ed. Engl., 1996, 35, 2638.
131. N. Agmon, Int. J. Chem. Kinet., 1981, 13, 333.
132. G. Huybrechts and B. Van Mele, Int. J. Chem. Kinet., 1994, 26, 333.