A theoretical study of the Favorskii rearrangement. Calculation of gas-phase reaction paths and solvation effects on the molecular mechanism for the transposition of the α-chlorocyclobutanone

Journal of the American Chemical Society

Volumn 119, Issue 8, 1997, Pages 1941-1947

  Moliner, V ^a   Castillo, R ^a   Safont, V S ^a   Oliva, M ^a   Bohn, S ^c   Tunon I ^b   Andres J ^a  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

^c INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANECARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; COMPUTER SIMULATION; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; REACTION ANALYSIS; THEORY;

EID: 0030934241     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962571q     Document Type: Article

References (86)

1. Favorskii, A. E. J. Russ. Phys. Chem. Soc. 1894, 26, 559.
2. Kende, A. S. Organic Reactions; 1960; Vol. 11, p 261.
3. Akhrem, A. A.; Ustynynk, T. K.; Titov, Y. A. Usp. Khim. 1970, 39, 1560.
4. Akhrem, A. A.; Ustynynk, T. K.; Titov, Y. A. Russ. Chem. Rev. 1970, 39, 732.
5. March, J. Advanced Organic Chemistry; New York, 1992; p 1080.
6. le Noble, W. J. Highlights of Organic Chemistry; New York, 1974; p 864.
7. Chenier, P. J. J. Chem. Ed. 1978, 55, 286-291.
8. Barbee, T. R.; Guy, H.; Heeg, M. J.; Albizati, K. F. J. Org. Chem. 1991, 56, 6773.
9. Satoh, T.; Oguro, K.; Shishikura, J. Tetrahedron Lett. 1992, 33, 1455.
10. Kimpe, N.; D'Hondt, L. L., M. Tetrahedron 1992, 48, 3183.
11. Satoh, T.; Oguro, K.; Shishikura, J. Bull. Chem. Soc. Jpn. 1993, 66, 2339.
12. Satoh, T.; Motohashi, S.; Kimura, S. Tetrahedron Lett. 1993, 34, 4823.
13. Lu, T.-J.; Liu, S.-W.; Wang, S.-H. J. Org. Chem. 1993, 58, 7945.
14. Llera, J. M.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5544.
15. Brik, M. E. Synthesis Commun. 1990, 20, 1487.
16. Lee, E.; Yoon, C. H. J. Chem. Soc., Chem. Commun. 1994, 4, 479.
17. Sosnovsky, G.; Cai, Z.-W. J. Org. Chem. 1995, 60, 3414.
18. Favorskii, A. E. J. Prakt. Chem. 1913, 88, 641.
19. Aston, E. A. J. Am. Chem. Soc. 1940, 62, 2590.
20. Stevens, C. L.; Malik, W.; Pratt, R. J. Am. Chem. Soc. 1950, 72, 4758.
21. Richard Compt. Rend. 1933, 197, 1943.
22. Tchoubar, B. Compt. Rend. 1949, 228, 580.
23. Tchoubar, B.; Sackur, O. Compt. Rend. 1939, 208, 1020.
24. Richard Compt. Rend. 1935, 200, 1944.
25. McPhee, W.; Klingsberg, E. J. Am. Chem. Soc. 1944, 66, 1132.
26. Loftfield, R. B. J. Am. Chem. Soc. 1950, 72, 632.
27. Loftfield, R. B. J. Am. Chem. Soc. 1951, 73, 4707.
28. Bordwell, F. G.; Strong, J. G. J. Org. Chem. 1973, 38, 579.
29. House, H. O.; Frank, G. A. J. Org. Chem. 1965, 30, 2948.
30. Vickers, S.; Smissman, E. E. J. Org. Chem. 1975, 40, 749.
31. Smissman, E. E.; Lemke, T. L.; Kristiansen, O. J. Am. Chem. Soc. 1966, 88, 334.
32. Selman, S.; Eastham, J. F. Quart. Rev. (London) 1960, 14, 221.
33. Warnhoff, E. W.; Wong, C. M.; Tai, W. T. J. Am. Chem. Soc. 1967, 17, 514.
34. Conia, J. M.; Salaün, J. Tetrahedron Lett. 1963, 1175.
35. Conia, J. M.; Salaün, J. Bull. Soc. Chim. France 1964, 1957.
36. Rappe, C.; Knutsson, L. Acta Chem. Scand. 1967, 21, 163.
37. Skancke, P. N. Acta. Chem. Scand. 1993, 47, 629.
38. Williams, I. H. Chem. Soc. Rev. 1993, 277.
39. Stewart, J. D.; Liotta, L. J.; Benkovic, S. J. Acc. Chem. Res. 1993, 26, 396.
40. Labonowsky, J. K.; Andzelm, J. Density Functional Methods in Chemistry; Springer-Verlag: New York, 1991.
41. Fan, L.; Ziegler, T. J. Chem. Phys. 1990, 92, 3645.
42. Fan, L.; Ziegler, T. J. Am Chem. Soc. 1992, 114, 10890.
43. Sosa, C.; Andzelm, J.; Elkin, B. C.; Wimmer, E.; Dobbs, K. D.; Dixon, D. A. J. Phys. Chem. 1992, 96, 6630.
44. Berces, A.; Ziegler, T. J. Chem. Phys. 1993, 98, 4793.
45. Handy, N. C.; Murray, C. W.; Amos, R. D. J. Phys. Chem. 1993, 97, 4392.
46. Seminario, J. M. Chem. Phys. Lett. 1993, 206, 547.
47. Johnson, B. G.; Gill, P. M. W.; Pople, J. A. J. Chem. Phys. 1993, 98, 5612.
48. Estrin, D. A.; Paglieri, L.; Corongiu, G. J. Phys. Chem. 1994, 98, 5653.
49. Carpenter, J. E.; Sosa, C. P. J. Mol. Struct. (Theochem) 1994, 311, 325.
50. Reichardt, C. Solvents and Solvent Effect in Organic Chemistry; 2nd ed.; Weinheim, 1988.
51. Andrés, J.; Bohm, S.; Moliner, V.; Silla, E.; Tuñón, I. J. Phys. Chem. 1994, 98, 6955.
52. Tuñón, I.; Silla, E.; Bertrán, J. J. Chem. Soc., Faraday Trans 1994, 90, 1757-1761.
53. Tomasi, T.; Persico, M. Chem. Rev. 1994, 94, 2027.
54. Tapia, O.; Goscinski, O. Mol. Phys. 1975, 29, 1653.
55. Tapia, O. Theoretical Models of Chemical Bonding; Maksic, Z. B., Ed.; Springer-Verlag: Berlin, 1992; p 435.
56. Andrés, J.; Queralt, J. J.; Safont, V. S.; Canle L., M.; Santaballa, J. A. J. Phys. Chem. 1996, 100, 3561.
57. Domingo, L. R.; Picher, M. T.; Andrés, J.; Moliner, V.; Safont, V. S. Tetrahedron 1996, 52, 10693.
58. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. GAUSSIAN94, Revision B.I; Gaussian, Inc.: Pittsburgh, PA, 1995.
59. Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
60. Andzelm, J.; Wimmer, E. J. Chem. Phys. 1992, 96, 1280.
61. Sim, F.; St-Amant, A.; Papai, I.; Salahub, D. R. J. Am. Chem. Soc. 1991, 114, 4391.
62. Gill, P. M. W.; Johnson, B. G.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1992, 197, 499.
63. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
64. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
65. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
66. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
67. Tapia, O.; Andres, J. Chem. Phys. Lett. 1984, 109, 471.
68. Andrés, J.; Moliner, V.; Safont, V. S. J. Chem. Soc., Faraday Trans. 1994, 90, 1703.
69. Tapia, O.; Andrés, J.; Safont, V. S. J. Chem. Soc., Faraday Trans. 1994, 90, 2365.
70. Baker, J. J. Comput. Chem. 1986, 7, 385.
71. Baker, J. J. Comput. Chem. 1987, 8, 563.
72. Fukui, K. J. Phys. Chem. 1970, 74, 4161.
73. González, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
74. González, C.; Schlegel, H. B. J. Chem. Phys. 1991, 95, 5853.
75. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
76. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676.
77. McIver, J. W. J. Acc. Chem. Res. 1974, 7, 72.
78. Rivail, J. L.; Rinaldi, D. Chem. Phys. 1976, 18, 233.
79. Rivail, J. L.; Terryn, D.; Rinaldi, D.; Ruiz-López, M. F. J. Mol. Struct., THEOCHEM 1985, 120, 387.
80. Rinaldi, D.; Rivail, J. L.; Rguini, N. J. J. Comput. Chem. 1992, 13, 675.
81. Rinaldi, R.; Pappalardo, R. R.: SCRFPAC, QCPE, Indiana University: Bloomington, EIN, 1992; Program number 622.
82. Frisch, M. J.; T., G. W.; Head-Gordon, M.; Gill, P. M.; 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. GAUSSIAN92, Revision G.I; Gaussian Inc, Pittsburgh, PA, 1992.
83. Dillet, V.; Rinaldi, D.; Angyan, J. G.; Rivail, J. L. Chem. Phys. Letters 1993, 202, 18.
84. Tuñon, I.; Rinaldi, D.; Ruiz-López, M. F.; Rivail, J. L. J. Phys. Chem. 1995, 99, 3798.
85. Pauling, L. J. Am. Chem. Soc. 1947, 69, 542.
86. Blake, J. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1991, 113, 7430.