Preference of Electron Transfer to Nucleophilic Addition in Reactions of Ketene Silyl Acetals with Quinones and Catalysis of Magnesium Ion

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 4, 1996, Pages 1107-1116

  Fujita, Morifumi ^a   Fukuzumi, Shunichi ^a   Matsubayashi, Gen Etsu ^a   Otera, Junzo ^b  

^a OSAKA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006312490     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1107     Document Type: Article

References (49)

1. S. Fukuzumi, M. Fujita, J. Otera, and Y. Fujita, J. Am. Chem. Soc., 114, 10271 (1992).
2. T. Sato, Y. Wakahara, J. Otera, H. Nozaki, and S. Fukuzumi, J. Am. Chem. Soc., 113, 4028 (1991); J. Otera, Y. Fujita, T. Sato, H. Nozaki, S. Fukuzumi, and M. Fujita, J. Org. Chem., 57, 5054 (1992).
3. T. Sato, Y. Wakahara, J. Otera, H. Nozaki, and S. Fukuzumi, J. Am. Chem. Soc., 113, 4028 (1991); J. Otera, Y. Fujita, T. Sato, H. Nozaki, S. Fukuzumi, and M. Fujita, J. Org. Chem., 57, 5054 (1992).
4. N. Kornblum, Angew. Chem., Int. Ed. Engl., 14, 734 (1975); S. F. Martin, Tetrahedron, 36, 419 (1980).
5. N. Kornblum, Angew. Chem., Int. Ed. Engl., 14, 734 (1975); S. F. Martin, Tetrahedron, 36, 419 (1980).
6. M. T. Reetz, K. Schwellnus, F. Hühner, W. Massa, and R. E. Schmidt, Chem. Ber., 116, 3708 (1983): G. E. Torten, G. Wenke, and Y. E. Rhodes, Synth. Commun., 15, 291 (1985);
7. M. T. Reetz, K. Schwellnus, F. Hühner, W. Massa, and R. E. Schmidt, Chem. Ber., 116, 3708 (1983): G. E. Torten, G. Wenke, and Y. E. Rhodes, Synth. Commun., 15, 291 (1985);
8. R. Rathore, Z. Lin, and J. K. Kochi, Tetrahedron Lett., 34, 1859 (1993);
9. T. M. Bockman, S. Perrier, and J. K. Kochi, J. Chem. Soc., Perkin Trans. 2, 1993, 595.
10. K. Narasaka, N. Arai, and T. Okauchi, Bull. Chem. Soc. Jpn., 66, 2995 (1993); K. Narasaka and Y. Kohno, Bull. Chem. Soc. Jpn., 66, 3456 (1993); Y. Kohno and K. Narasaka, Bull. Chem. Soc. Jpn., 68, 322 (1995); E. Baciocchi, A. Casu, and R. Ruzziconi, Tetrahedron Lett., 28, 3707 (1989).
11. K. Narasaka, N. Arai, and T. Okauchi, Bull. Chem. Soc. Jpn., 66, 2995 (1993); K. Narasaka and Y. Kohno, Bull. Chem. Soc. Jpn., 66, 3456 (1993); Y. Kohno and K. Narasaka, Bull. Chem. Soc. Jpn., 68, 322 (1995); E. Baciocchi, A. Casu, and R. Ruzziconi, Tetrahedron Lett., 28, 3707 (1989).
12. K. Narasaka, N. Arai, and T. Okauchi, Bull. Chem. Soc. Jpn., 66, 2995 (1993); K. Narasaka and Y. Kohno, Bull. Chem. Soc. Jpn., 66, 3456 (1993); Y. Kohno and K. Narasaka, Bull. Chem. Soc. Jpn., 68, 322 (1995); E. Baciocchi, A. Casu, and R. Ruzziconi, Tetrahedron Lett., 28, 3707 (1989).
13. K. Narasaka, N. Arai, and T. Okauchi, Bull. Chem. Soc. Jpn., 66, 2995 (1993); K. Narasaka and Y. Kohno, Bull. Chem. Soc. Jpn., 66, 3456 (1993); Y. Kohno and K. Narasaka, Bull. Chem. Soc. Jpn., 68, 322 (1995); E. Baciocchi, A. Casu, and R. Ruzziconi, Tetrahedron Lett., 28, 3707 (1989).
14. A. Bhattacharya, L. M. DiMichele, U.-H. Dolling, E. J. J. Grabowski, and V. J. Grenda, J. Org. Chem., 54, 6118 (1989).
15. A. Pross and S. S. Shaik, Acc. Chem. Res., 16, 363 (1983); A. Pross, Acc. Chem. Res., 18, 212 (1985); S. S. Shaik, Prog. Phys. Org. Chem., 15, 197 (1985); J. K. Kochi, Angew. Chem., Int. Ed. Engl., 27, 1227 (1988); J.-M. Mattalia, B. Vacher, A. Samat, and M. Chanon, J. Am. Chem. Soc., 114, 4111 (1992).
16. A. Pross and S. S. Shaik, Acc. Chem. Res., 16, 363 (1983); A. Pross, Acc. Chem. Res., 18, 212 (1985); S. S. Shaik, Prog. Phys. Org. Chem., 15, 197 (1985); J. K. Kochi, Angew. Chem., Int. Ed. Engl., 27, 1227 (1988); J.-M. Mattalia, B. Vacher, A. Samat, and M. Chanon, J. Am. Chem. Soc., 114, 4111 (1992).
17. A. Pross and S. S. Shaik, Acc. Chem. Res., 16, 363 (1983); A. Pross, Acc. Chem. Res., 18, 212 (1985); S. S. Shaik, Prog. Phys. Org. Chem., 15, 197 (1985); J. K. Kochi, Angew. Chem., Int. Ed. Engl., 27, 1227 (1988); J.-M. Mattalia, B. Vacher, A. Samat, and M. Chanon, J. Am. Chem. Soc., 114, 4111 (1992).
18. A. Pross and S. S. Shaik, Acc. Chem. Res., 16, 363 (1983); A. Pross, Acc. Chem. Res., 18, 212 (1985); S. S. Shaik, Prog. Phys. Org. Chem., 15, 197 (1985); J. K. Kochi, Angew. Chem., Int. Ed. Engl., 27, 1227 (1988); J.-M. Mattalia, B. Vacher, A. Samat, and M. Chanon, J. Am. Chem. Soc., 114, 4111 (1992).
19. A. Pross and S. S. Shaik, Acc. Chem. Res., 16, 363 (1983); A. Pross, Acc. Chem. Res., 18, 212 (1985); S. S. Shaik, Prog. Phys. Org. Chem., 15, 197 (1985); J. K. Kochi, Angew. Chem., Int. Ed. Engl., 27, 1227 (1988); J.-M. Mattalia, B. Vacher, A. Samat, and M. Chanon, J. Am. Chem. Soc., 114, 4111 (1992).
20. U. Eisner and J. Kuthan, Chem. Rev., 72, 1 (1972); D. M. Stout and A. I. Meyers, Chem. Rev., 82, 223 (1982).
21. U. Eisner and J. Kuthan, Chem. Rev., 72, 1 (1972); D. M. Stout and A. I. Meyers, Chem. Rev., 82, 223 (1982).
22. S. Fukuzumi, "Advances in Electron Transfer Chemistry," ed by P. S. Mariano, JAI Press, Greenwich (1992), Vol. 2, p. 65; S. Fukuzumi and T. Tanaka, "Photoinduced Electron Transfer," ed by M. A. Fox and M. Chanon, Elsevier, Amsterdam (1988), Part C, Chap. 10.
23. S. Fukuzumi, "Advances in Electron Transfer Chemistry," ed by P. S. Mariano, JAI Press, Greenwich (1992), Vol. 2, p. 65; S. Fukuzumi and T. Tanaka, "Photoinduced Electron Transfer," ed by M. A. Fox and M. Chanon, Elsevier, Amsterdam (1988), Part C, Chap. 10.
24. S. Fukuzumi, S. Koumitsu, K. Hironaka, and T. Tanaka, J. Am. Chem. Soc., 109, 305 (1987), and references cited therein.
25. J. W. Bunting, Bioorg. Chem., 19, 456 (1991), and references cited therein.
26. S. Fukuzumi, N. Nishizawa, and T. Tanaka. J. Chem. Soc., Perkin Trans. 2, 1985, 371.
27. S. Fukuzumi and T. Okamoto, J. Am. Chem. Soc., 115, 11600 (1993);
28. S. Fukuzumi and T. Okamoto, J. Chem. Soc., Chem. Commun., 1994, 521.
29. A preliminary report has appeared; S. Fukuzumi, M. Fujita, G. Matsubayashi, and J. Otera, Chem. Lett., 1993, 1451.
30. R. E. Ireland, P. Wipf, and J. D. Armstrong, III, J. Org. Chem., 56, 650 (1991); C. Gennari, M. G. Beretta, A. Bernardi, G. Moro, C. Scolastico, and R. Todeschini, Tetrahedron, 42, 893 (1986); J. Otera, Y. Fujita, and S. Fukuzumi, Synlett, 1994, 213.
31. R. E. Ireland, P. Wipf, and J. D. Armstrong, III, J. Org. Chem., 56, 650 (1991); C. Gennari, M. G. Beretta, A. Bernardi, G. Moro, C. Scolastico, and R. Todeschini, Tetrahedron, 42, 893 (1986); J. Otera, Y. Fujita, and S. Fukuzumi, Synlett, 1994, 213.
32. R. E. Ireland, P. Wipf, and J. D. Armstrong, III, J. Org. Chem., 56, 650 (1991); C. Gennari, M. G. Beretta, A. Bernardi, G. Moro, C. Scolastico, and R. Todeschini, Tetrahedron, 42, 893 (1986); J. Otera, Y. Fujita, and S. Fukuzumi, Synlett, 1994, 213.
33. D. D. Perrin, W. L. F. Armarego, and D. R. Perrin, "Purification of Laboratory Chemicals," Pergamon Press, Elmsford (1966).
34. C. T. North, D. C. Phillips, and F. C. Matheus, Acta Crystallogr., Sect. A, 24A, 351 (1968).
35. M. Main, S. E. Hull, L. Lessinger, G. Germain, J.-P. Declercq, and M. M. Woolfson, "A System of Computer Programs of Crystal Structures from X-Ray Diffraction Data, MULTAN 78," University of York (1978).
36. "International Tables for X-Ray Crystallography," Kynoch Press, Birminbham (1974), Vol. 4.
37. R. Foster, "Organic Charge Transfer Complexes," Academic Press, New York (1969); R. Foster, "Molecular Complexes," Crane Russak and Co., New York (1974), Vol. 2, p. 108.
38. R. Foster, "Organic Charge Transfer Complexes," Academic Press, New York (1969); R. Foster, "Molecular Complexes," Crane Russak and Co., New York (1974), Vol. 2, p. 108.
39. H. A. Benesi and J. H. Hildebrand, J. Am. Chem. Soc., 71, 2703 (1949).
40. S. Fukuzumi and J. K. Kochi, J. Phys. Chem., 85, 648 (1981).
41. a for the SCE reference in MeCN is 4.40 V.
42. S. Fukuzumi and J. K. Kochi, J. Am. Chem. Soc., 102, 2141 (1980).
43. D. H. Evans, "Encyclopedia of Electrochemistry of the Elements, Organic Section," ed by A. J. Bard and H. Lund, Marcel Dekker, New York (1978), Chap. XII-1, and references cited therein.
44. K. Mikami, S. Matsumoto, A. Ishida, S. Takamuku, T. Suenobu, and S. Fukuzumi, J. Am. Chem. Soc., 117, 11134 (1995).
45. A. Rehm and A. Weller, Isr. J. Chem., 8, 259 (1970).
46. S. Fukuzumi, C. L. Wong, and J. K. Kochi, J. Am. Chem. Soc., 102, 2928 (1980).
47. S. Fukuzumi, M. Fujita, and J. Otera, J. Org. Chem., 58, 5405 (1993).
48. L. Meites, "Polarographic Techniques," 2nd ed, Wiley, New York (1965), pp. 203-301.
49. S. Fukuzumi, K. Ishikawa, K. Hironaka, and T. Tanaka, J. Chem. Soc., Perkin Trans. 2, 1987, 751.