Kinetic, thermodynamic and mechanistic studies on the reduction of carbenium ions by NAD(P)H analogues

Journal of Physical Organic Chemistry

Volumn 10, Issue 7, 1997, Pages 577-584

  Cheng, Jin Pei ^a   Lu, Yun ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Carbenium ions; NAD(P)H analogues; Reduction

Indexed keywords

EID: 0343222656     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(199707)10:7<577::AID-POC920>3.0.CO;2-T     Document Type: Article

References (40)

1. S. Fukuzumi, S. Koumitsu, K. Hironaka and T. Tanaka, J. Am. Chem. Soc. 109, 305-316 (1987), and references cited therein.
2. D. Mauzerall and F. H. Westheimer, J. Am. Chem. Soc. 77, 2261-2264 (1955).
3. S. Yasui, K. Nakamura and A. Ohno, J. Org. Chem. 49, 878-882 (1984).
4. S. Yausi, K. Nakamura, A. Ohno and S. Oka, Bull. Chem. Soc. Jpn. 55, 196-199 (1982).
5. J. J. Steffens and D. M. Chipman, J. Am. Chem. Soc. 93, 6694-6696 (1971).
6. (a) M. F. Powell, J. C. Wu and T. C. Bruice, J. Am. Chem. Soc. 106, 3850-3856 (1984);
7. (b) B. W. Carlson and L. L. Miller, J. Am. Chem. Soc. 105, 7453-7454 (1983);
8. (c) S. Fukuzumi and Y. Tokuda, J. Phys. Chem. 97, 3738-3741 (1993);
9. (d) J.-M. Saveant, Acc. Chem. Res. 26, 455-461 (1993);
10. (e) W. Adam, M. Heil and R. Hutterer, J. Org. Chem. 57, 4491-4495 (1992);
11. (f) Y. Ohnishi and A. Ohno, Chem. Lett. 697-700 (1976);
12. (g) A. Ohno, H. Yamamoto and S. Oka, Bull. Chem. Soc. Jpn. 54, 3489-3491 (1981);
13. (h) S. Fukuzumi and M. Chiba, J. Chem. Soc., Perkin Trans. 2, 1393-1398 (1991).
14. S. Yausi and A. Ohno, Bioorg. chem. 14, 70-96 (1986).
15. M. F. Powell and T. C. Bruice, J. Am. Chem. Soc. 105, 1014-1021, 7139-7149 (1983).
16. B. W. Carlson, L. L. Miller, P. Neta and J. Grodkowski, J. Am. Chem. Soc. 106, 7233-7239 (1984).
17. J. W. Bunting, Bioorg. Chem. 19, 456-491 (1991).
18. J. W. Bunting and S. Sindhuatmadji, J. Org. Chem. 46, 4211-4219 (1981).
19. R. M. G. Roberts, D. Ostovic and M. M. Kreevoy, J. Org. Chem. 48, 2053-2056 (1983).
20. A. Singer and M. McElvain, Org. Synth. 14, 30-31 (1934).
21. H. J. Dauben, L. R. Honen and K. M. Harmon, J. Org. Chem. 25, 1442-1445 (1960).
22. W. S. Matthews, J. E. Bares, J. E. Bartmess, F. G. Bordwell, F. G. Cornforth, G. E. Drucker, Z. Margolin, R. J. McCollum, G. J. McCollum and N. R. Vanier, J. Am. Chem. Soc. 97, 7006-7014 (1975).
23. (a) J.-P. Cheng and Y. Zhao, Tetrahedron 121, 5267-5276 (1994);
24. (b) J.-P. Cheng, Y. Zhao and Z. Huan, Sci. China (Ser. B) 38, 1417-1424 (1995).
25. J. W. Bunting and M. M. Conn, Can. J. Chem. 68, 537-542 (1990).
26. A. M. P. Nicholas and D. R. Arnold, Can. J. Chem. 60, 2165-2179 (1982).
27. J.-P. Cheng, PhD Dissertation, Northwestern University, Evanston, IL (1987).
28. (a) F. G. Bordwell and M. J. Bausch, J. Am. Chem. Soc. 108, 2473-2474 (1986);
29. (b) F. G. Bordwell, J.-P. Cheng and M. J. Bausch, J. Am. Chem. Soc. 110, 2867-2872 (1988);
30. (c) F. G. Bordwell, J.-P. Cheng and M. J. Bausch, J. Am. Chem. Soc. 110, 2872-2877 (1988);
31. (d) F. G. Bordwell and J.-P. Cheng, J. Am. Chem. Soc. 111, 1792-1795 (1989).
32. V. D. Parker, J. Am. Chem. Soc. 114, 7458-7462 (1992); 115, 1201 (1993) (erratum).
33. V. D. Parker, J. Am. Chem. Soc. 114, 7458-7462 (1992); 115, 1201 (1993) (erratum).
34. (a) J.-P. Cheng, K. L. Handoo and V. D. Parker, J. Am. Chem. Soc. 115, 2655-2660 (1993);
35. (b) K. L. Handoo, J.-P. Cheng and V. D. Parker, J. Am. Chem. Soc. 115, 5067-5072 (1993).
36. Unpublished results from this laboratory.
37. (a) M. C. A. Donkersloot and H. M. Buck, J. Am. Chem. Soc. 103, 6554-6558 (1981);
38. (b) Y.-D. Wu, D. K. W. Lai and K. N. Houk, J. Am. Chem. Soc. 117, 4100-4108 (1995).
39. R. A. Marcus, J. Phys. Chem. 72, 891-899 (1968).
40. M. Ishikawa, S. Fukuzumi, T. Goto and T. Tanaka, Bull. Chem. Soc. Jpn. 62, 3754-3756 (1989).