Evaluation of the relative magnitude of the β-effect of silicon and the γ-effect of tin by intermolecular competition

Bulletin of the Chemical Society of Japan

Volumn 73, Issue 5, 2000, Pages 1253-1257

  Sugawara, Masanobu ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; SILANE DERIVATIVE; SILICON; TIN;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION;

EID: 0034037514     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.73.1253     Document Type: Article

References (73)

1. For example: a) J. B. Lambert, Y. Zhao, R. W. Emblide, L. A. Salvador, X. Liu, J.-H. So, and E. C. Chelius, Acc. Chem. Res., 32, 183 (1999).
2. b) J. Yoshida and K. Nishiwaki, J. Chem. Sac., Dalton Trans., 1998, 2589.
3. c) J. M. White, Aust. J. Chem., 48, 1227 (1995).
4. d) J. R. Hwu, B.-L. Chen, and S.-S. Shiao, J. Org. Chem., 60, 2448 (1995).
5. e) J. Yoshida, T. Murata, S. Matsunaga, T. Maekawa, S. Shiozawa, and S. Isoe, Rev. Heterotaom. Chem.. 5, 193 (1991).
6. f) J. B. Lambert, Tetrahedron, 46, 2677 (1990).
7. g) Y. Apeloig, "The Chemistry of Organic Silicon Compounds," ed by S. Patai and Z. Rappoport, Wiley, Chichester (1989), p. 57.
8. h) J. C. Giordan, J. Am. Chem. Soc., 105, 6544 (1983).
9. Synthetic applications of the β-effect of silicon: For example: a) W. P. Weber, "Silicon Reagents for Organic Synthesis," Springer-Verlag, Berlin and Heidelberg (1983).
10. b) E. W. Colvin, "Silicon Reagents in Organic Synthesis," ed Academic Press, London (1988).
11. c) I. Fleming, in "Comprehensive Organic Synthesis," ed by B. M. Trost, I. Fleming, and L. A. Paquette, Pergamon Press, Oxford (1991), Vol. 2, p. 563.
12. d) I. Fleming, J. Dunoguès, and R. Smithers, Org. React., 37, 57 (1989).
13. Synthetic applications of the β-effect of tin: For example: a) M. Pereyre, J.-B. Quintard, and A. Rahm, "Tin in Organic Synthesis," Butterworth & Co., London (1987).
14. b) Y. Yamamoto, Aldrichimica Acta, 20, 45 (1987).
15. Synthetic applications of the γ-effect of silicon: For example: a) H. Sakurai, T. Imai, and A. Hosomi, Tetrahedron Lett., 1977, 4045.
16. b) Y. Hatanaka and I. Kuwajima, Tetrahedron Lett., 27, 719 (1986).
17. Synthetic applications of the γ-effect of tin: a) D. D. Davis, R. L. Chambers, and H. T. Johnson, J. Organomet. Chem., 25, C13 (1970).
18. b) T. Sato, Synthesis. 1990, 259.
19. c) L. Plamondon and J. D. Wuest, J. Org. Chem., 56, 2066 and 2076 (1991 ).
20. d) J. A. Marshall, J. A. Jablonowski, and G. P. Luke, J. Org. Chem., 59, 7825 (1994).
21. e) T. Sato and S. Nagatsuka, Synlett, 653 (1995).
22. f) R. L. Beddoes, M. L. Lewis, P. Quayle, and S. Johal, Tetrahedron Lett., 36, 471 (1995).
23. g) N. Isono and M. Mori, J. Org. Chem., 61, 7867 (1996).
24. h) H. Wakamatsu, N. Isono, and M. Mori, J. Org. Chem., 62, 8917 (1997).
25. i) A. Krief and L. Provins, Tetrahedron Lett., 39, 2017 (1998).
26. a) R. S. Brown, D. F. Eaton, A. Hosomi, T. G. Traylor, and J. M. Wright, J. Organomet. Chem., 66, 249 (1974).
27. b) J. B. Lambert and R. B. Finzel, J. Am. Chem. Soc., 104, 2020 (1982).
28. c) S. G. Wierschke, J. Chandrasekhar, and W. L. Jorgensen, J. Am. Chem. Soc., 107, 1496 (1985).
29. d) N. Auner, R. Walsh, and J. Westrup, J. Chem. Soc., Chem. Commun., 1986, 207.
30. e) P. Magnus, P. M. Cairns, and J. Moursounidis, J. Am. Chem. Soc., 109, 2469 (1987).
31. f) J. B. Lambert, G. Wang, R. B. Finzel, and D. H. Teramura, J. Am. Chem. Soc., 109, 7838 (1987).
32. g) D. Hajdasz and R. Squires, J. Chem. Soc., Chem. Commun., 1988, 1212.
33. h) J. B. Lambert, G. Wang, and D. H. Teramura, J. Org. Chem., 53, 5422 (1988).
34. i) X. Li and J. A. Stone, J. Am. Chem. Soc., 111, 5586 (1989).
35. j) J. B. Lambert and E. C. Chelius, J. Am. Chem. Soc., 112, 8120 (1990).
36. k) M. A. Brook and A. Neuy, J. Org. Chem., 55, 3609 (1990).
37. l) J. Yoshida, T. Maekawa, T. Murata, S. Matsunaga, and S. Isoe, J. Am. Chem. Soc., 112, 1962 (1990).
38. m) H.-U. Siehl, F.-P. Kaufmann, Y. Apeloig, V. Braude, D. Danovich, A. Berndt, and N. Stamatis, Angew. Chem., Int. Ed. Engl., 30, 1479 (1991).
39. n) G. Hage and H. Mayr, J. Am. Chem. Soc., 113, 4954 (1991).
40. o) J. M. White and G. B. Robertson, J. Org. Chem., 57, 4638 (1992).
41. p) J. B. Lambert, R. W. Emblidge, and S. Malany, J. Am. Chem. Soc., 115, 1317 (1993).
42. q) V. Gabelica and A. J. Kresge, J. Am. Chem. Soc., 118, 3838 (1996).
43. r) V. Y. Chan, C. I. Clark, J. Giordano, A. J. Green, A. Karalis, and J. M. White, J. Org. Chem., 61, 5227 (1996).
44. a) H. G. Kuivila and N. M. Scarpa, J. Am. Chem. Soc., 92, 6990 (1970).
45. b) H. C. Clark and R. C. Poller, Can. J. Chem., 48, 2670 (1970).
46. c) D. D. Davis and H. T. Johnson, J. Am. Chem. Soc., 96, 7576 (1974).
47. d) D. C. McWilliam, T. R. Balasubramanian, and H. G. Kuivila, J. Am. Chem. Soc., 100, 6407 (1978).
48. e) V. J. Shiner, Jr., M. W. Ensinger, and G. S. Kriz, J. Am. Chem. Soc., 108, 842 (1986).
49. f) E. R. Davidson and V. J. Shiner, Jr., J. Am. Chem. Soc., 108, 3135 (1986).
50. g) J. Cooper and V. J. Shiner, Jr., J. Org. Chem., 54, 4270 (1989).
51. h) I. Fleming, S. K. Patel, and C. J. Urch, J. Chem. Soc., Perkin Trans. 1, 1989, 115.
52. i) V. J. Shiner, Jr., and M. W. Ensinger, J. Org. Chem., 55, 653 (1990).
53. j) J. Cooper, V. J. Shiner, Jr., and M. W. Ensinger, J. Am. Chem. Soc., 112, 2834 (1990).
54. k) J. B. Lambert, L. A. Salvador, and J.-H. So, Organometallics, 12. 697 (1993).
55. l) A. J. Green, T. Pigdon, J. M. White, and J. Yamen, J. Org. Chem., 63, 3943 (1998).
56. m) T. Nakashima, R. Fujiyama, M. Fujio, and Y. Tsuno, Tetrahedron Lett., 40, 539 (1999).
57. n) T. Nakashima, R. Fujiyama, M. Fujio, and Y. Tsuno, Bull. Chem. Soc. Jpn., 12, 1043 (1999).
58. o) T. Nakashima, R. Fujiyama, M. Fujio, and Y. Tsuno, Bull. Chem. Soc. Jpn., 72, 741 (1999).
59. M. Sugawara and J. Yoshida, J. Am. Chem. Soc., 119, 11986 (1997).
60. a) M. Sugawara and J. Yoshida, Synlett, 1998, 1057.
61. b) M. Sugawara and J. Yoshida, Tetrahedron Lett., 40, 1717 (1999).
62. Reactivity of group 14 elements substituted olefins toward electrophiles: a) J. Bartl, S. Steenken, and H. Mayr, J. Am. Chem. Soc., 113, 7710 (1991).
63. b) H. Mayr and M. Patz, Angew. Chem., Int. Ed. Engl., 33, 938 (1994).
64. c) H. Mayr, O. Kuhn, M. F. Gotta, and M. J. Patz, Phys. Org. Chem., 11, 642 (1998).
65. Sugawara and J. Yoshida, J. Chem. Soc., Chem. Commun., 1999, 505.
66. A. Hosomi, M. Endo, and H. Sakurai, Chem. Lett., 1976, 941.
67. Oxidation potential of allylsilanes. See: J. Yoshida, T. Murata, and S. Isoe, Tetrahedron Lett., 27, 3373 (1986).
68. Reactions of homoallylstannanes with hetero electrophiles have been reported. a) D. J. Peterson and M. D. Robbins, Tetrahedron Lett., 1972, 2135.
69. b) D. J. Paterson, M. D. Robbins, and J. R. Hansen, J. Organomet. Chem., 73, 237 (1974).
70. c) K. C. Nicolaou, D. A. Claremon, W. E. Barnette, and S. P. Seitz, J. Am. Chem. Soc., 101, 3704 (1979).
71. d) Y. Ueno, M. Ohta, and M. Okawara, Tetrahedron Lett., 23, 2577 (1982).
72. e) J. W. Herndon and J. J. Harp, Tetrahedron Lett., 33, 6243 (1992).
73. "Gaussian 98 (Revision, A. 6)," M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, 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. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian, Inc., Pittsburgh, PA (1998).