The β-silicon effect. II. Substituent effects on the solvolysis of 1-aryl-2-(aryldimethylsilyl)ethyl 3,5-dinitrobenzoates

Bulletin of the Chemical Society of Japan

Volumn 79, Issue 7, 2006, Pages 1091-1099

  Fujio, Mizue ^a   Umezaki, Yuzo ^b   Alam, Md Ashadul ^a   Kikukawa, Kiyoshi ^b   Fujiyama, Ryoji ^c   Tsuno, Yuho ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b KINKI UNIVERSITY   (Japan)

^c KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ETHANOL; SOLUTIONS; SUBSTITUTION REACTIONS; SUBSTRATES;

SILYLATION; SOLVOLYSIS;

ESTERS;

1 (3 CHLORO 4 METHOXYPHENYL) 2 (DIMETHYLPHENYLSILYL)ETHYL 3,5 DINITROBENZOIC ACID; 1 (3 CHLOROPHENYL) 2 (DIMETHYLPHENYLSILYL)ETHYL 3,5 DINITROBENZOIC ACID; 1 (4 CHLOROPHENYL) 2 (DIMETHYLPHENYLSILYL)ETHYL 3,5 DINITROBENZOIC ACID; 1 [3,5 BIS(TRIFLUOROMETHYL)PHENYLDIMETHYLSILYL] 1 (3 CHLORO 4 METHOXYPHENYL)ETHYL 3,5 DINITROBENZOIC ACID; 2 (DIMETHYLPHENYLSILYL) 1 (3 METHYLPHENYL)ETHYL 3,5 DINITROBENZOIC ACID; 2 (DIMETHYLPHENYLSILYL) 1 (4 METHYLPHENYL)ETHYL 3,5 DINITROBENZOIC ACID; 2 (DMETHYLPHENYLSILYL) 1 [3 (TRIFLUOROMETHYL)PHENYL]ETHYL 3,5 DINITROBENZOIC ACID; 2 [3,5 BIS(TRIFLUOROMETHYL)PHENYLDIMETHYLSILYL] 1 (4 METHYLPHENYL)ETHYL 3,5 DINITROBENZOIC ACID; 2 [3,5 BIS(TRIFLUOROMETHYL)PHENYLDIMETHYLSILYL] 1 [3 (TRIFLUOROMETHYL)PHENYL]ETHYL 3,5 DINITROBENZOIC ACID; ALCOHOL; NITROBENZOIC ACID DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SILYLATION; SOLVOLYSIS; SYNTHESIS;

EID: 33750602653     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.79.1091     Document Type: Article

References (37)

1. For part 1: M. Fujio, M. Uchida, A. Okada, M. A. Alam, R. Fujiyama, H.-U. Siehl, Y. Tsuno, Bull. Chem. Soc. Jpn. 2005, 78, 1834.
2. a) J. B. Lambert, G.-t. Wang, R. B. Finzel, D. H. Teramura, J. Am. Chem. Soc. 1987, 109, 7838.
3. b) J. B. Lambert, E. C. Chelius, J. Am. Chem. Soc. 1990, 112, 8120;
4. J. B. Lambert, R. W. Emblidge, S. Malany, J. Am. Chem. Soc. 1993, 115, 1317.
5. Y. Apeloig, The Chemistry of Organic Silicon Compounds, ed. by S. Patai, Z. Rappoport, John Wiley & Sons, Chichester, 1989, Chap. 2, p. 57, and references cited therin.
6. a) J. B. Lambert, Tetrahedron 1990, 46, 2677;
7. N. Shimizu, Rev. Heteroat. Chem. 1993, 9, 155.
8. b) J. B. Lambert, Y. Zhao, R. W. Emblidge, L. A. Salvador, X. Liu, J.-H. So, E. C. Chelius, Acc. Chem. Res. 1999, 32, 183.
9. a) N. Shimizu, S. Watanabe, Y. Tsuno, Bull. Chem. Soc. Jpn. 1991, 64, 2249.
10. b) N. Shimizu, C. Kinoshita, E. Osajima, F. Hayakawa, Y. Tsuno, Bull. Chem. Soc. Jpn. 1991, 64, 3280.
11. c) N. Shimizu, S. Watanabe, F. Hayakawa, S. Yasuhara, Y. Tsuno, T. Inazu, Bull. Chem. Soc. Jpn. 1994, 67, 500.
12. a) Y. Yukawa, Y. Tsuno, Bull. Chem. Soc. Jpn. 1959, 32, 971;
13. Y. Yukawa, Y. Tsuno, M. Sawada, Bull. Chem. Soc. Jpn. 1966, 39, 2274;
14. Y. Tsuno, M. Fujio, Chem. Soc. Rev. 1996, 25, 129.
15. b) Y. Tsuno, M. Fujio, Adv. Phys. Org. Chem. 1999, 32, 267.
16. E. Grunwald, S. Winstein, J. Am. Chem. Soc. 1948, 70, 846;
17. F. L. Schadt, T. W. Bentley, P. v. R. Schleyer, J. Am. Chem. Soc. 1976, 98, 7667;
18. T. W. Bentley, G. E. Carter, J. Am. Chem. Soc. 1982, 104, 5741;
19. T. W. Bentley, G. Llewellyn, Prog. Phys. Org. Chem. 1990, 17, 121.
20. Y. Tsuno, Y. Kusuyama, M. Sawada, T. Fujii, Y. Yukawa, Bull. Chem. Soc. Jpn. 1975, 48, 3337;
21. M. Fujio, T. Adachi, Y. Shibuya, A. Murata, Y. Tsuno, Tetrahedron Lett. 1997, 25, 4557;
22. E. A. Hill, M. L. Gross, M. Stasiewicz, M. Manion, J. Am. Chem. Soc. 1969, 91, 7381.
23. I. Lee, Adv. Phys. Org. Chem. 1992, 27, 57.
24. G. S. Hammond, J. Am. Chem. Soc. 1955, 77, 334;
25. J. E. Leffler, E. Grunwald, Rates and Equilibria of Organic Reactions, Wiley, New York, 1963;
26. E. S. Lewis, C. C. Shen, R. A. More O'Ferrall, J. Chem. Soc., Perkin Trans. 2 1981, 1084.
27. P. G. Gassman, A. F. Fentiman, Jr., J. Am. Chem. Soc. 1970, 92, 2549;
28. P. G. Gassman, A. F. Fentiman, Jr., J. Am. Chem. Soc. 1969, 91, 1545;
29. P. G. Gassman, J. Zeller, J. T. Lumb, J. Chem. Soc., Chem. Commun. 1968, 69.
30. I. Mihel, M. Orlovic, E. Polla, S. Borcic, J. Org. Chem. 1979, 44, 4086;
31. I. Mihel, J. Sistek, S. Borcic, K. Humsky, D. E. Sunko, J. Org. Chem. 1979, 44, 4091.
32. H. C. Brown, E. N. Peters, J. Am. Chem. Soc. 1975, 97, 1927;
33. H. C. Brown, M. Ranvindranathan, J. Am. Chem. Soc. 1977, 99, 299.
34. C. Lim, S.-H. Kim, S.-D. Yoh, M. Fujio, Y. Tsuno, Tetrahedron Lett. 1997, 38, 3243.
35. S. H. Kim, S.-D. Yoh, M. Fujio, H. Imahori, M. Mishima, Y. Tsuno, Bull. Korean Chem. Soc. 1995, 16, 760;
36. S.-H. Kim, S.-D. Yoh, C. Lim, M. Mishima, M. Fujio, Y. Tsuno, J. Phys. Org. Chem. 1998, 11, 254.
37. H. Gilman, L. Tolman, F. Yeoman, L. A. Woods, D. A. Shirley, S. Avakinan, J. Am. Chem. Soc. 1946, 68, 426.