Calculated effect of substitutions on the regioselectivity of cyclization of α-sulfenyl-, α-sulfinyl-, and α-sulfonyl-(5R)-5-hexenyl radicals

Journal of Organic Chemistry

Volumn 71, Issue 26, 2006, Pages 9595-9601

  Wu, Ching Wen ^a   Ho, Jia Jen ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; ELECTRONS; REACTION KINETICS; SUBSTITUTION REACTIONS;

MOIETIES; RADICALS; REGIOSELECTIVITY;

FREE RADICALS;

ALPHA SULFENYL 5 HEXENYL RADICAL; ALPHA SULFENYL 5 METHYL 5 HEXENYL RADICAL; ALPHA SULFINYL 5 HEXENYL RADICAL; ALPHA SULFINYL 5 METHYL 5 HEXENYL RADICAL; ALPHA SULFONYL 5 AMINE 5 HEXENYL RADICAL; ALPHA SULFONYL 5 HEXENYL RADICAL; ALPHA SULFONYL 5 METHYL 5 HEXENYL RADICAL; AMMONIA; CYANIDE; HEXANE; METHYL GROUP; NITROGEN DIOXIDE; RADICAL; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PARAMETERS; CHEMICAL REACTION; CYCLIZATION; ENERGY; ENTHALPY; MATHEMATICAL ANALYSIS; REACTION ANALYSIS; REGIOSELECTIVITY; RING CLOSING METATHESIS; SUBSTITUTION REACTION;

EID: 33845942274     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061614a     Document Type: Article

References (76)

1. Bennasar, M. L.; Juan, C.; Bosch, J. Chem. Commun. 2000, 2459.
2. Ellis, D. A.; Hart, D. J.; Zhao, L. Tetrahedron Lett. 2000, 41, 9357.
3. Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 4883.
4. Haney, B. P.; Curran, D. P. J. Org. Chem. 2000, 65, 2007.
5. Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; pp 162-283.
6. (a) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073 and references therein.
7. (b) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
8. Surzur, J. M. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum: New York, 1981; Vol. 2, Chapter 3.
9. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317.
10. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
11. (a) Leach, A. G.; Wang, R.; Wohlhieter, G. E.; Khan, S. I.; Jung, M. E.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 4271.
12. (b) Della, E. W.; Kostakis, C.; Smith, P. A. Org. Lett. 1999, 1, 363.
13. (c) Jursic, B. S. THEOCHEM 1999, 492, 285.
14. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
15. Dolbier, W. R., Jr. Chem. Rev. 1996, 96, 1557 and references therein.
16. Dolbier, W. R., Jr.; Rong, X. X.; Bartgerger, M. D.; Koroniak, H.; Smart, B. E.; Yang, Z.-Y. J. Chem. Soc., Perkin Trans. 1998, 2, 219.
17. Dolbier, W. R., Jr.; Rong, X. X.; Smart, B. E.; Yang, Z.-Y. J. Org. Chem. 1996, 61, 4824.
18. Dolbier, W. R., Jr.; Li, A.; Smart, B. E.; Yang, Z.-Y. J. Org. Chem. 1998, 63, 5687.
19. Li, A.; Shatrev, A. B.; Smart, B. E.; Yang, Z.-Y.; Lusztyk, J.; Ingold, K. U.; Bravo, A.; Dolbier, W. R., Jr. J. Org. Chem. 1999, 64, 5993.
20. (a) Beckwith, A. L. J.; Blair, I. A.; Phillipou, G. Tetrahedron Lett. 1974, 2251.
21. (b) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun. 1974, 472.
22. Beckwith, A. L. J.; Lawrence, T. J. Chem. Soc., Perkin Trans. 2 1979, 1535.
23. (a) Della, E. W.; Smith, P. A. J. Chem. Soc., Perkin Trans. 1 2001, 445.
24. (b) Della, E. W.; Smith, P. A. Tetrahedron Lett. 2001, 42, 481.
25. (c) Della, E. W.; Smith, P. A. J. Org. Chem. 2000, 65, 6627.
26. (d) Della, E. W.; Smith, P. A. J. Org. Chem. 1999, 64, 1798.
27. (e) Della, E. W.; Knill, A. M.; Smith, P. A. Chem. Commun. 1996, 14, 1637.
28. (f) Della, E. W.; Knill, A. M. Tetrahedron Lett. 1996, 37, 5805.
29. (g) Della, E. W.; Knill, A. M. J. Org. Chem. 1996, 61, 7529.
30. (h) Della, E. W.; Knill, A. M. Aust. J. Chem. 1995, 48, 2047.
31. (a) Wilt, J. J. Org. Chem. 1981, 103, 5251;
32. Tetrahedron 1985, 41, 3979.
33. (b) Wilt, J. W.; Lustztyk, J.; Peeran, M.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 281.
34. (a) Tsai, Y.-M.; Chang, F.-C.; Huang, L.; Shiu, C.-L. Tetrahedron Lett. 1989, 30, 2121.
35. (b) Ke, B.-W.; Lin, C.-H.; Tsai, Y.-M. Tetrahedron 1997, 53, 7805.
36. (c) Ke, B.-W.; Lin, C.-H.; Tsai, Y.-M. Tetrahedron Lett. 1990, 31, 6047.
37. (a) Renaud, P. Tetrahedron Lett. 1990, 31, 4601.
38. (b) Clive, D. L. L.; Boivin, T. L. B. J. Org. Chem. 1989, 54, 1997.
39. (c) Reutrakul, V.; Poolsanong, C.; Pohmakotr, M. Tetrahedron Lett. 1989, 30, 6913.
40. Della, E. W.; Graney, S. D. J. Org. Chem. 2004, 69, 3824-3835.
41. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976.
42. 1 = 0.23).
43. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 4th ed.; Kluwer Academic/Plenum Publishers: New York. 2000; Part A.
44. (a) Marcus, R. A. J. Chem. Phys. 1956, 24, 966.
45. (b) Marcus, R. A. Annu. Rev. Phys. Chem. 1964, 15, 155.
46. (c) Marcus, R. A. J. Phys. Chem. 1968, 72, 891.
47. (d) Chen, M. Y.; Murdoch, J. R. J. Am. Chem. Soc. 1984, 106, 4735 and references therein.
48. (a) Magnoli, D. E.; Murdoch, J. R. J. Am. Chem. Soc. 1981, 103, 7465.
49. (b) Murdoch, J. R.; Magnoli, D. E. J. Am. Chem. Soc. 1982, 104, 3792.
50. (c) Wolf, S.; Mitchell, J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694.
51. (a) Anglada, J. M.; Domingo, V. M. J. Phys. Chem. A 2005, 109, 10786.
52. (b) Zhang, W.; Du, B. THEOCHEM 2006, 760, 131.
53. Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136B, 864.
54. Kohn, W.; Sham, L. J. Phys. Rev. 1965, A1133.
55. (a) Becke, A. D. J. Chem. Phys. 1992, 96, 2155.
56. (b) Becke, A. D. J. Chem. Phys. 1992, 97, 9173.
57. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
58. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
59. Lee, C.; Wang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
60. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
61. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian Inc.: Pittsburgh, PA, 1998.
62. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
63. (a) Curtiss, L. A.; Redfern, P. C.; Raghavachari, K.; Rassolov, V.; Pople, J. A. J. Chem. Phys. 1999, 110, 4703.
64. (b) Baboul, A. G.; Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem. Phys. 1999, 110, 7650.
65. (c) Janoschek, R.; Rossi, M. Int. J. Chem. Kinet. 2002, 34, 550.
66. Weinhold, F.; Landis, C. R. Chem. Educ. Res. Pract. 2001, 2, 91.
67. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
68. Carpenter, J. E.; Weinhold, F. J. Mol. Struct. 1988, 169, 41.
69. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736.
70. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
71. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066.
72. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211.
73. Creary, X. In Substituent Effects in Radical Chemistry; Viehe, H. G., Ed.; Reidel Publishing Co.: New York, 1986; p 245.
74. Bordwell, F. G.; Liu, W.-Z. J. Phys. Org. Chem. 1998, 11, 397.
75. Paquette, L. Synlett 2001, 1, 1.
76. Craig, S. L.; Zhong, M.; Choo, B.; Brauman, J. I. J. Phys. Chem. A 1997, 101, 19.