Theoretical study of the reaction mechanism of the uncatalyzed epoxidation of alkenes by iodosylbenzene

New Journal of Chemistry

Volumn 27, Issue 5, 2003, Pages 811-817

  Barea, Guada ^a   Maseras, Feliu ^a   Lledós, Agustí ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZENE DERIVATIVE; ETHYLENE; IODOSOBENZENE; MONOMER; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; EPOXIDATION; HYDRATION; PRIORITY JOURNAL;

EID: 84962345543     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b203861g     Document Type: Article

References (58)

1. K. Weissermel and H.-J. Arpe, Industrial Organic Chemistry, Wiley-VCH, New York, 3rd edn., 1997.
2. S. J. Lippard and J. M. Berg, Bioinorganic Chemistry, University Science Books, Mill Valley, CA, 1994.
3. (a) W. Adam, C. M. Mitchell and C. R. Saha-Möller, J. Org. Chem., 1999, 64, 3699;
4. (b) W. Adam and T. Wirth, Acc. Chem. Res., 1999, 32, 703.
5. (a) W. Adam and B. Nestler, Tetrahedron Lett., 1993, 34, 611;
6. (b) W. Adam and A. K. Smerz, Tetrahedron, 1995, 51, 13039;
7. (c) H. Yao and D. E. Richardson, J. Am. Chem. Soc., 2000, 122, 3220.
8. (a) C. C. Romão, F. E. Kühn and W. A. Herrmann, Chem. Rev., 1997, 97, 3197;
9. (b) G. Wahl, D. Kleinhenz, A. Schorm, J. Sundermeyer, R. Stowasswer, C. Rumney, G. Bringmann, C. Fickert and W. Kiefer, Chem.-Eur. J., 1999, 5, 3237.
10. K. N. Houk, K. R. Condroski and W. A. Pryor, J. Am. Chem. Soc., 1996, 118, 13002.
11. (a) R. D. Bach, C. M. Estévez, J. E. Winter and M. N. Glukhovtsev, J. Am. Chem. Soc., 1998, 120, 680;
12. (b) R. D. Bach, M. N. Glukhovtsev and C. Gonzalez, J. Am. Chem. Soc., 1998, 120, 9902.
13. W. Adam, R. D. Bach, O. Dmitrenko and C. R. Saha-Möller, J. Org. Chem., 2000, 65, 6715.
14. (a) P. Gisdakis, S. Antonczak, S. Köstlemeier, W. A. Herrmann and N. Rösch, Angew. Chem., Int. Ed., 1998, 37, 2211;
15. (b) C. D. Valentin, R. Gandolfi, P. Gisdakis and N. Rösch, J. Am. Chem. Soc., 2001, 123, 2365.
16. (a) D. V. Deubel, J. Sundermeyer and G. Frenking, Inorg. Chem., 2000, 39, 2314;
17. (b) D. V. Deubel, J. Sundermeyer and G. Frenking, J. Am. Chem. Soc., 2000, 122, 10 101.
18. D. G. Musaev, H. Basch and K. Morokuma, J. Am. Chem. Soc., 2002, 124, 4135.
19. J. T. Groves and R. S. Myers, J. Am. Chem. Soc., 1983, 105, 5791.
20. (a) A. F. Tai, L. D. Margerum and J. S. Valentine, J. Am. Chem. Soc., 1986, 108, 5006;
21. (b) W. Nam and J. S. Valentine, J. Am. Chem. Soc., 1990, 112, 4977;
22. (c) Y. Yang, F. Diederich and J. S. Valentine, J. Am. Chem. Soc., 1991, 113, 7195.
23. (a) E. G. Samsel, K. Srinivasan and J. K. Kochi, J. Am. Chem. Soc., 1985, 107, 7606;
24. (b) E. N. Jacobsen, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH: New York, 1993, p. 159;
25. (c) T. Katsuki, Coord. Chem. Rev., 1995, 140, 189.
26. (a) Z. Gross and S. Ini, J. Org. Chem., 1997, 62, 5514;
27. (b) Z. Gross, A. Simkhovich and N. Galili, Chem. Commun., 1999, 599.
28. (a) A. Stassinopoulos and J. P. Caradonna, J. Am. Chem. Soc., 1990, 112, 7071;
29. (b) S. Mukerjee, A. Stassinopoulos and J. P. Caradonna, J. Am. Chem. Soc., 1997, 119, 8097.
30. (a) J. T. Groves, R. C. Haushalter, M. Nakamura, T. E. Nemo and B. J. Evans, J. Am. Chem. Soc., 1981, 103, 2884;
31. (b) D. Feichtinger and D. A. Plattner, Angew. Chem., Int. Ed. Engl., 1997, 109, 1796;
32. (c) N. Jin and J. T. Groves, J. Am. Chem. Soc., 1999, 121, 2923.
33. (a) C. Linde, B. Åkermark, P.-O. Norrby and M. Svensson, J. Am. Chem. Soc., 1999, 121, 5083;
34. (b) Y. G. Abashkin, J. R. Collins and S. K. Burt, Inorg. Chem., 2001, 40, 4040.
35. (a) L. Cavallo and H. Jacobsen, Angew. Chem., Int. Ed., 2000, 39, 589;
36. (b) H. Jacobsen and L. Cavallo, Chem.-Eur. J., 2001, 7, 800.
37. (a) S. P. de Visser, F. Ogliaro, N. Harris and S. Shaik, J. Am. Chem. Soc., 2001, 123, 3037;
38. (b) F. Ogliaro, S. P. de Visser, S. Cohen, P. K. Sharma and S. Shaik, J. Am. Chem. Soc., 2002, 124, 2806.
39. J. D. Koola and J. K. Kochi, J. Org. Chem., 1987, 52, 4545.
40. W. Nam and J. S. Valentine, J. Am. Chem. Soc., 1993, 115, 1772.
41. S. Mukerjee, K. Skogerson, S. DeGala and J. P. Caradonna, Inorg. Chim. Acta, 2000, 297, 313.
42. (a) A. Varvoglis, Hyspervalent Iodine in Organic Synthesis, Academic Press, San Diego, CA, 1997;
43. (b) P. J. Stang, P. J. and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123.
44. (a) D. Macikenas, W. Skrzypczak-Jankun and J. D. Protasiewicz, J. Am. Chem. Soc., 1999, 121, 7164;
45. (b) D. Macikenas, W. Skrzypczak-Jankun and J. D. Protasiewicz, Angew. Chem., Int. Ed., 2000, 39, 2007.
46. V. E. Mylonas, M. P. Sigalas, G. A. Katsoulos, C. A. Tsipis and A. G. Varvoglis, J. Chem. Soc., Perkin Trans. 2, 1994, 1691.
47. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. res, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian 98, Gaussian, Inc., Pittsburgh, PA, 1998.
48. W. R. Wadt and P. J. Hay, J. Chem. Phys., 1985, 82, 284.
49. A. Höllwarth, M. Böhme, S. Dapprich, A. W. Ehlers, A. Gobbi, V. Jonas, K. F. Köhler, R. Stegmann, A. Veldkamp and G. Frenking, Chem. Phys. Lett., 1993, 208, 237.
50. W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257.
51. P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213.
52. R. Krishnan, J. S. Binkley, R. Seeger and J. A. Pople, J. Chem. Phys., 1980, 72, 650.
53. S. Miertus, E. Scrocco and J. Tomasi, Chem. Phys., 1981, 55, 117.
54. A. Misra, R. J. Berry and P. Marshall, J. Phys. Chem. A, 1997, 101, 7420.
55. C. J. Carmalt, J. G. Crossley, J. G. Knight, P. Lightfoot, A. Martin, M. P. Muldowney, N. C. Norman and A. G. Orpen, J. Chem. Soc., Chem. Commun., 1994, 2367.
56. H. W. Richter, B. R. Cherry, T. D. Zook and G. F. Koser, J. Am. Chem. Soc., 1997, 119, 9614.
57. C. Gonzalez and H. B. Schlegel, J. Phys. Chem., 1990, 94, 5523.
58. R. D. Bach, M. N. Glukhovtsev, C. Gonzalez, M. Marquez, C. M. Estévez, A. G. Baboul and H. B. Schlegel, J. Phys. Chem. A, 1997, 101, 6092.