Pericyclic and pseudopericyclic thermal cheletropic decarbonylations: When can a pericyclic reaction have a planar, pseudopericyclic transition state?

Journal of the American Chemical Society

Volumn 119, Issue 19, 1997, Pages 4509-4517

  Birney, David M ^a   Ham, Sihyun ^a   Unruh, Gregory R ^a,b  

^a TEXAS TECH UNIVERSITY   (United States)

^b Tech Spray   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CONFORMATIONAL TRANSITION; CYCLIZATION;

EID: 0030978884     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963551r     Document Type: Article

References (96)

1. Portions of this work were previously reported. Sihyun Ham, David M. Birney, Pacifichem, 1995, Honolulu, Hawaii.
2. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie, GmbH: Weinheim, 1970.
3. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper and Row, Publishers: New York, 1987; p 839.
4. Ross, J. A.; Seiders, R. P.; Lemal, D. M. J. Am. Chem. Soc. 1976, 98, 4325-4327.
5. 6
6. Wentrup, C.; Netsch, K. P. Angew. Chem., Int. Ed. Engl. 1984, 23, 802.
7. Bevan, J. W.; Legon, A. C. J. Chem. Soc., Faraday Trans. 2 1973, 69, 902-925.
8. 9
9. Halevi, E. A. Orbital Symmetry and Reaction Mechanism. The OCAMS View., 1st ed.; Springer-Verlag: New York, 1992.
10. 11 for hydrocarbon pericyclic reaction, as a direct cosequence of the need for cyclic orbital overlap.
11. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682-708.
12. (a) Birney, D. M; Wagenseller, P. E. J. Am. Chem. Soc. 1994, 116, 6262-6270.
13. (b) Ham, S.; Birney, D. M. Tetrahedron Lett. 1994, 35, 8113-8116.
14. (c) Wagenseller, P. E.; Birney, D. M.; Roy, D. J. Org. Chem. 1995, 60, 2853-2859.
15. (d) Ham, S.; Birney, D. M. J. Org. Chem. 1996, 61, 3962-3968.
16. (e) Birney, D. M. J. Org. Chem. 1996, 61, 243-251.
17. (f) Matsui, H.; Zuckerman, E. J.; Katagiri, N.; Sugihara, T.; Kaneko, C.; Ham, S.; Birney, D. M. J. Phys. Chem. In press.
18. 9
19. (a) Zimmerman, H. E. Acc. Chem. Res. 1971, 4, 272.
20. (b) Dewar, M. J. S. Angew. Chem., Int. Ed. Engl. 1971, 10, 761.
21. Fukui, K. Acc. Chem. Res. 1971, 4, 57.
22. 9
23. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736.
24. 19
25. Chen, C.; Quinn, E. K.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1993, 58, 5011-5014.
26. Birney, D. M. J. Org. Chem. 1994, 59, 2557-2564.
27. 12c
28. 23
29. Lopez, S.; Rodriguez, J.; Rey, J. G.; Lera, A. R. d. J. Am. Chem. Soc. 1996, 118, 1881-1891.
30. 4 work, see ref 25.
31. Snyder, J. P.; Halgren, T. A. J. Am. Chem. Soc. 1980, 102, 2861-2863.
32. Mock, W. L. In Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Organic Reactions; Academic Press: New York, 1977; Vol. 35, Part 2, pp 141-197.
33. (a) Lewis, J. D.; Laane, J. Spectrochim. Acta 1975, 31A, 755-763.
34. (b) Gordon, R. D.; Orr, D. R. J. Mol. Spectrosc. 1988, 129, 24-44.
35. (c) Bencivenni, L.; Ramondo, F.; Quirante, J. J. J. Mol. Struct. (Theochem) 1995, 330, 389-393.
36. (d) Quirante, J. J.; Enriquez, F. Theor. Chim. Acta 1994, 89, 251-259.
37. (e) Rzepa, H. S. J. Chem. Res. (S) 1988, 224-225.
38. (f) Unruh, G. R. Ph.D. Thesis, Texas Tech University, 1995.
39. (a) Simpson, C. J. S. M.; Price, J.; Holmes, G.; Adam, W.; Martin, H.-D.; Bish, S. J. Am. Chem. Soc. 1990, 112, 5089-5094.
40. (b) Jimenez, R.; Kable, S. H.; Loison, J.-C.; Simpson, C. J. S. M.; Adam, W.; Houston, P. L. J. Phys. Chem. 1992, 96, 4188-4195.
41. (c) Prather, K. A.; Rosenfeld, R. N. J. Phys. Chem. 1991, 95, 6544-6548.
42. Wentrup, C.; Heilmayer, W.; Kollenz, G. Synthesis 1994, 1219-1248.
43. (a) Fulloon, B. E.; Wentrup, C. J. Org. Chem. 1996, 61, 1363-1368.
44. (b) Fulloon, B.; El-Nabi, H. A. A.; Kollenz, G.; Wentrup, C. Tetrahedron Lett. 1995, 36, 6547-6550.
45. (c) Kappe, C. O.; Kollenz, G.; Leung-Toung, R.; Wentrup, C. J. Chem. Soc., Chem. Commun. 1992, 487-490.
46. (d) Maslivets, A. N.; Krasnykh, O. P.; Smirnova, L. I.; Andreichikov, Y. S. J. Org. Chem. (USSR) 1989, 941-948.
47. (a) Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81.
48. (b) Jiao, H.; Schleyer, P. v. R. Angew, Chem., Int. Ed. Engl. 1995, 34, 334-337.
49. (c) Jiao, H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1995, 117, 11529-11535.
50. 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. In Gaussian, Inc.; Pittsburgh, PA, 1992.
51. The dipole moments are consistently smaller in the transition structures, which reflects the reversed dipole moment of carbon monoxide.
52. Kappe, C. O.; Wong, M. W.; Wentrup, C. J. Org. Chem. 1995, 60, 1686-1695.
53. Pople, J. A.; Scott, A. P.; Wong, M. W.; Radom, L. Isr. J. Chem. 1993, 33, 345.
54. 37 They aer used here as a simple means to identify electrophilic and nucleophilic sites.
55. Williams, D. E. In Reviews in Computational Chemistry; Boyd, D., Lipkowitz, K., Eds.; Wiley Interscience: New York, 1991; pp 219-271.
56. Dunning, T. H.; Hay, P. J. Modern Theoretical Chemistry; Plenum: New York, 1976.
57. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley and Sons: New York, 1986.
58. Hammond, G. S. J. J. Am. Chem. Soc. 1955, 77, 334.
59. (a) Bell, R. P. Proc. R. Soc. London, Ser. A 1936, 154, 414.
60. (b) Evans, M. G.; Polanyi, M. Trans. Faraday. Soc. 1938, 34, 11-29.
61. Birney, D. M.; Berson, J. A. Tetrahedron 1986, 42, 1561-1570.
62. In this correlation, the pericyclic loop consisted of only carbon atoms.
63. Spangler, R. J.; Beckmann, B. G.; Kim, J. H. J. Org. Chem. 1977, 42, 2989-2996.
64. 11,46 we did not pursue this calculation further.
65. Birney, D. M.; Wiberg, K. B.; Berson, J. A. J. Am. Chem. Soc. 1988, 110, 6631-6642.
66. Dolbier, W. R., Jr.; Frey, H. M. J. Chem. Soc., Perkin Trans. 2 1974, 1674.
67. Buxton, J. P.; Simpson, C. J. S. M. Chem. Phys. 1986, 105, 307-316.
68. (a) Clarke, S. C.; Johnson, B. L. Tetrahedron 1971, 25, 3555-3561.
69. (b) Battiste, M. A.; Visnick, M. Tetrahedron Lett. 1978, 4771-4774.
70. (a) LeBlanc, B. F.; Sheridan, R. S. J. Am. Chem. Soc. 1985, 107, 4554-4555.
71. (b) Birney, D. M.; Berson, J. A. J. Am. Chem. Soc. 1985, 107, 4553-4554.
72. (a) Nakumura, K.; Koda, S.; Akita, K. Bull. Chem. Soc. Jpn. 1978, 51, 1665.
73. (b) Darling, T. R.; Pouliquen, J.; Turro, N. J. J. Am. Chem. Soc. 1974, 96, 1247.
74. (a) Turro, N. J.; Hammond, W. B. J. Am. Chem. Soc. 1966, 88, 3672-3673.
75. (b) Rodriquez, H. J.; Chang, J.-C.; Thomas, T. F. J. Am. Chem. Soc. 1976, 98, 2027-2034.
76. Pazos, J. F.; Pacifici, J. G.; Pierson, G. O.; Sclove, P. B.; Greene, F. D. J. Org. Chem. 1974, 39, 1990.
77. (a) Yamabe, S.; Minato, T.; Osamura, Y. J. Am. Chem. Soc. 1979, 101, 4525-4531.
78. (b) Sevin, A.; Fazilleau, E.; Chaquin, P. Tetrahedron 1981, 37, 3831-3837.
79. Pochan, J. M.; Baldwin, J. E.; Flygare, W. H. J. Am. Chem. Soc. 1969, 91, 1896-1898.
80. Staley, S. W., Norden, T. D.; Taylor, W. H.; Harmony, M. D. J. Am. Chem. Soc. 1987, 109, 7641-7647.
81. 58
82. Aliev, Z. G.; Maslivets, A. N.; Simonchik, O. L.; Konyukhova, T. G.; Andreichikov, Y. S.; Atovmyan, L. O. Russ. Chem. Bull. 1995, 44, 1496-1498.
83. 11 and the results reported here are no exception.
84. Arenas, J. F.; Quirante, J. J.; Ramirez, F. J. J. Mol. Struct. (Theochem) 1989, 183, 143-150.
85. Bierbach, A.; Barnes, I.; Becker, K.; Wiesen, E. Environ. Sci. Technol. 1994, 28, 715-729.
86. 63
87. (a) Loncharich, R. J.; Brown, F. K.; Houk, K. N. J. Org. Chem. 1989, 54, 1129-1134.
88. (b) Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127-4133.
89. (c) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122-1127.
90. (a) Ralph, J.; Hatfield, R. D. J. Agric. Food Chem. 1991, 39, 1426-1437.
91. (b) Quinkert, G.; Grosso, M. d.; Bucher, A.; Bauch, M.; Doring, W.; Bats, J. W.; Durner, G. Tetrahedron Lett. 1992, 33, 3617-3620.
92. Berstermann, H.-M.; Harder, R.; Winter, H.-W.; Wentrup, C. Angew. Chem., Int. Ed. Engl. 1980, 19, 564-565.
93. 67
94. (a) Gong, L.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1991, 113, 6021-6028.
95. (b) Wong, M. W.; Wentrup, C. J. Org. Chem. 1994, 59, 5279-5285.
96. Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487-7492.