Mechanism of Methoxide Ion Substitution in the Z and E Isomers of O-Methylbenzohydroximoyl Halides

Journal of Organic Chemistry

Volumn 69, Issue 8, 2004, Pages 2741-2749

  Johnson, James E ^a   Dolliver, Debra D ^b,d   Yu, Lonchun ^a   Canseco, Diana C ^a   McAllister, Michael A ^b,e   Rowe, Jeffrey E ^c  

^a TEXAS WOMAN'S UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH TEXAS   (United States)

^c LA TROBE UNIVERSITY   (Australia)

^d SOUTHEASTERN LOUISIANA UNIVERSITY   (United States)

^e AGOURON PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHEMICAL ACTIVATION; CHEMICAL BONDS; ENTROPY; ISOMERS; NITROGEN; ROTATION; STEREOCHEMISTRY;

STEREOMUTATION; SUBSTITUTION PRODUCTS;

SUBSTITUTION REACTIONS;

CARBON; DIMETHYL SULFOXIDE; FLUORIDE; HALIDE; HYDROXIMOYL FLUORIDE; METHANOL; METHOXIDE SODIUM; METHYL GROUP; NITROGEN; O METHYLBENZOHYDROXIMOYL HALIDE; OXIDE; SODIUM DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; COVALENT BOND; ENTROPY; ISOMER; KINETICS; REACTION ANALYSIS; ROTATION; STEREOCHEMISTRY; STEREOSPECIFICITY; SUBSTITUTION REACTION;

EID: 1842739380     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030299e     Document Type: Article

References (53)

1. Rappoport, Z. Acc. Chem. Res. 1992, 25, 474-479.
2. Youssef, A. A.; Sharaf, S. M.; El-Sadany, S. K.; Hamed, E. A. J. Org. Chem. 1981, 46, 3813-3816.
3. Rappoport, Z. Rec. Trav. Chim. 1985, 104, 309-349.
4. Maffeo, C. B.; Marchese, G.; Naso, F.; Ronzini, L. J. Chem. Soc., Perkin Trans. 1 1979, 92-97.
5. Dodd, D.; Johnson, M. D.; Meeks, B. S.; Titchmarsh, D. M.; Van Duong, K. N.; Gaudemer, A. J. Chem. Soc., Perkin Trans. 2 1976, 1261-1267.
6. Glukhovtsev, M. N.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1994, 116, 5961-5962.
7. Kim, C. K.; Hyun, K. H.; Kim, C. K.; Lee, I. J. Am. Chem. Soc. 2000, 122, 2294-2299.
8. Li, H. G.; Kim, C. K.; Lee, B.; Kim, C. K.; Rhee, S. K.; Lee, I. J. Am. Chem. Soc. 2001, 123, 2326-2333.
9. Okuyama, T.; Takino, T.; Sato, K.; Ochiai, M. J. Am. Chem. Soc. 1998, 120, 2275-2282.
10. Williams, A. Acc. Chem. Res. 1989, 22, 387-392.
11. Castro, E. A.; Cubillos, M.; Santos, J. G. J. Org. Chem. 1998, 63, 6820-6823.
12. Castro, E. A.; Pavez, P.; Santos, J. G. J. Org. Chem. 1999, 64, 2310-2313.
13. Stefanidis, D.; Cho, S.; Dhe-Paganon, S.; Jencks, W. P. J. Am. Chem. Soc. 1993, 115, 1650-1656.
14. Ba-Saif, S. A.; Colthurst, M.; Waring, M. A.; Williams, A. J. Chem. Soc., Perkin Trans. 2 1991, 1901-1908.
15. Kevill, D. N.; Oldfield, A. J.; D'Souza, M. J. J. Chem. Res., Synop. 1996, 122-123.
16. Bentley, T. W.; Llewellyn, G.; McAlister, J. A. J. Org. Chem. 1996, 61, 7927-7932.
17. Hengge, A. C.; Hess, R. A. J. Am. Chem. Soc. 1994, 116, 11256-11263.
18. Hengge, A. J. Am. Chem. Soc. 1992, 114, 6575-6576.
19. (a) Johnson, J. E.; Riesgo, E. C.; Jano, I. J. Org. Chem. 1996, 61, 45-50.
20. (b) Johnson, J. E.; Cornell, S. C. J. Org. Chem. 1980, 45, 4144-4148.
21. Hegarty, A. F.; Cronin, J. D.; Scott, F. L. J. Chem. Soc., Perkin Trans. 2 1975, 429.
22. Salvelova, V. A.; Popov, A. F. Russ. J. Org. Chem. 1999, 35, 797-828.
23. Johnson, J. E.; Jano, I.; McAllister, M. A. J. Phys. Org. Chem. 1999, 12, 240-246.
24. Rowe, J. E.; Lee, K. Aust. J. Chem. 1997, 50, 849-852.
25. Rowe, J. E.; Papanelopoulos, D. A. Aust. J. Chem. 1995, 48, 2041-2046.
26. Johnson, J. E.; Todd, S. L.; Gardner, J. L.; Gardner, T. M.; Buck, P.; Ghafouripour, A.; Zimmerman, W. J. Phys. Org. Chem. 1994, 7, 352-358.
27. Johnson, J. E.; Todd, S. L.; Dutson, S. M.; Ghafouripour, A.; Alderman, R. M.; Hotema, M. R. J. Org. Chem. 1992, 57, 4648-4653.
28. Rowe, J. E.; Hegarty, A. F. J. Org. Chem. 1984, 49, 3083-3087.
29. Johnson, J. E.; Nalley, E. A.; Weidig, C.; Arfan, M. J. Org. Chem. 1981, 46, 3623-3629.
30. Rappoport, Z.; Topol, A. J. Chem. Soc., Perkin Trans. 2 1975, 863-874.
31. Bunnett, J. F.; Garbisch, E. W., Jr.; Pruitt, K. M. J. Am. Chem. Soc. 1957, 79, 385-391.
32. Marchese, G.; Naso, F.; Modena, G. J. Chem. Soc. B 1969, 290-293.
33. Silversmith, E. F.; Smith, D. J. Org. Chem. 1958, 23, 427-430.
34. Ta-Shma, R.; Rappoport, A. J. Am. Chem. Soc. 1977, 99, 1845-1858.
35. Hegarty, A. F.; McCormack, M. T.; Hathaway, B. J.; Hulett, L. J. Chem. Soc., Perkin Trans. 2 1977, 1136-1141.
36. Hoz, S.; Basch, H.; Wolk, J. L.; Rappoport, Z.; Goldberg, M. J. Org. Chem. 1991, 56, 5424-5426.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakzewski, 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.; Repogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Degrees, D. J.; Baker, J.; Head-Gordon, S. M.; Gonzales, C.; Pople, J. A. Gaussian 94, Revision D.3; Gaussian: Pittsburgh, PA, 1996.
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakzewski, V. G.; Montgomery, J. A.; Jr.; Stratman, R. E. ; Burant, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennuci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morojuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.9; Gaussian: Pittsburgh, PA, 1998.
39. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986; and references therein.
40. (a) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974-12979.
41. (b) Parr, R. G.; Yang W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
42. (c) Dreizler, R. M.; Gross E. K. V. Density Functional Theory; Springer, Berlin, 1990.
43. (d) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3105.
44. (e) Lee, C.; Yang, W.; Parr R. G. Phys. Rev. B 1988, 37, 785-790.
45. (a) Forseman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, J. J. Phys. Chem. 1996, 100, 16098-16102.
46. (b) Tomasi, J.; Bonaccorsi, R.; Cammi, R.; Valle, F. J. O. THEOCHEM 1991, 234, 401-402.
47. Sakamoto, T.; Okamoto, K.; Kikugawa, Y. J. Org. Chem. 1992, 57, 3245-3248.
48. Rowe, J. E.; Lee, K.; Dolliver, D. D.; Johnson, J. E. Aust. J. Chem. 1999, 52, 807-811.
49. Gould, E. S. Mechanism and Structure in Organic Chemistry; Holt, Rinehart, and Winston: Chicago, 1959; p 173.
50. Johnson, J. E.; Nalley, E. A.; Kunz, Y. K.; Springfield, J. R. J. Org. Chem. 1976, 41, 252-259.
51. Beart, P. M.; Ward, A. D. Aust. J. Chem. 1974, 27, 1341-1349.
52. Leggio, A.; Liguori, A.; Sicilliano, C.; Sindona, G. J. Org. Chem. 2001, 66, 2246-2250.
53. Johnson, J. E.; Springfield, J. R.; Hwang, J. S.; Hayes, L. J.; Cunningham, W. C.; McClaugherty, D. L. J. Org. Chem. 1971, 36, 284-294.