Investigation of the [Sm{N(SiMe3)2}2] reducing system in THF. Rate and mechanistic studies

Journal of the American Chemical Society

Volumn 124, Issue 49, 2002, Pages 14663-14667

  Prasad, Edamana ^a   Knettle, Brian W ^a   Flowers II, Robert A ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LOW ACTIVATION BARRIERS;

ABSORPTION; CYCLIC VOLTAMMETRY; IODINE COMPOUNDS; KETONES; RATE CONSTANTS; REDUCTION; ULTRAVIOLET SPECTROGRAPHS;

SAMARIUM COMPOUNDS;

2 BUTANONE; ACETIC ACID DERIVATIVE; BUTANE; IODINE DERIVATIVE; KETONE DERIVATIVE; REDUCING AGENT; SAMARIUM;

ARTICLE; CYCLIC POTENTIOMETRY; OXIDATION REDUCTION REACTION; REACTION TIME; REDUCTION; ULTRAVIOLET SPECTROSCOPY;

EID: 0037065311     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028111g     Document Type: Article

References (42)

1. This paper is dedicated to Professor John W. Larsen in deep appreciation for his mentoring, advice, and friendship.
2. Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
3. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943.
4. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
5. Molander, G. A. Chem. Rev. 1992, 92, 29.
6. Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485.
7. Inanaga, J.; Yokoyama, Y.; Baba, Y.; Yamaguchi, M. Tetrahedron Lett. 1991, 32, 5559.
8. Kamochi, Y.; Kudo, T. Tetrahedron 1992, 48, 4301.
9. Kamochi, Y.; Kudo, T. Tetrahedron Lett. 1991, 32, 3511.
10. Ogawa, A.; Sumino, Y.; Nanke, T.; Ohya, S.; Sonada, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 2745.
11. Molander, G. A.; McKie, J. A. J. Org. Chem. 1992, 57, 3132.
12. For crystallographic studies, see: Hou, Z.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205,
13. Hou, Z.; Zhang, Y.; Wakatsuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149-153. For solution studies, see:
14. Shotwell, J. B.; Sealy, J. M.; Flowers, R. A., II. J. Org. Chem. 1999, 64, 5251.
15. Knettle, B. W.; Flowers, R. A. II. Org. Lett. 2001, 3, 2321.
16. Enemaerke, R. J.; Hertz, T.; Skrydstrup, T.; Daasbjerg, K. Chem.-Eur. J. 2000, 6, 3747.
17. Haesegawa, E.; Curran, D. P. J. Org. Chem. 1993, 58, 5008.
18. Cabri, W.; Candiani, I.; Colombo, M.; Franzoi, L.; Bedeschi, A. Tetrahedron Lett. 1995, 36, 949.
19. Newcomb, M.; Kaplan, J. Tetrahedron Lett. 1988, 29, 3449.
20. Namy, J.-L.; Colomb, M.; Kagan, H. B. Tetrahedron Lett. 1994, 35, 1723.
21. Hamann, B.; Namy, J.-L.; Kagan, H. B. Tetrahedron 1996, 52, 14225.
22. Kunishima, M.; Yoshimura, K.; Nakata, D.; Hioki, K.; Tani, S. Chem. Pharm. Bull. 1999, 47, 1196.
23. Kunishima, M.; Hioki, K.; Tani, S; Kato, A. Tetrahedron Lett. 1994, 35, 7253.
24. Kunishima, M.; Hioki, K.; Kono, K.; Sakuma, T.; Tani, S. Chem. Pharm. Bull 1994, 42, 2190.
25. Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219.
26. Evans, W. J.; Drummond, D. K.; Zhang, H.; Atwood, J. L. Inorg. Chem. 1988, 27, 575.
27. Brady, E. D.; Clark, D. L.; Keogh, D. W.; Scott, B. L.; Watkin, J. G. J. Am. Chem. Soc. 2000, 122, 7007.
28. Curran, D. P.; Gu, X.; Zhang, W.; Dowd, P. Tetrahedron 1997, 53, 9023.
29. Pedersen, S. U.; Lurid, T.; Daasbjerg, K.; Pop, M.; Fussing, I.; Lund, H. Acta Chem. Scand. 1998, 52, 657.
30. Shabangi, M.; Kuhlman, M. L.; Flowers, R. A., II. Org. Lett. 1999, 1, 2133.
31. Enemaerke, R. J.; Daasbjerg, K.; Skrydstrup, T. Chem. Commun. 1999, 343.
32. Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895.
33. Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6357.
34. Evans, W. J.; Gummersheimer, T. S.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 8999.
35. 2}. Details are contained in ref 19.
36. Okaue, Y.; Isobe, T. Inorg. Chem. Acta 1988, 144, 143.
37. McClure, D. S.; Kiss, Z. J. Chem. Phys. 1963, 39, 3251.
38. Johnson, K. E.; Sandoe, J. N. J. Chem. Soc. A 1960, 1694.
39. Kamenskaya, A. N. Russ. J. Inorg. Chem. 1984, 29, 251.
40. Hubig, S. M.; Rathore, R.; Kochi, J. K. J. Am. Chem. Soc. 1999, 121, 617.
41. Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050.
42. Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943.