Reducing characteristics of borohydride exchange resin-CuSO4 in methanol

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 5, 1997, Pages 1101-1107

  Sim, Tae Bo ^a   Yoon, Nung Min ^a  

^a Sogang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC EPOXIDES; AZOXYBENZENES; BOROHYDRIDES; BROMOBENZENE; CARBON-CARBON DOUBLE BONDS; CARBONYL GROUPS; CHEMO-SELECTIVITY; DIPHENYL DISULFIDE; DOUBLE BONDS; ELEVATED TEMPERATURE; EXCHANGE RESIN; NITROSOBENZENES; PHENYL AZIDE; PYRIDINE N-OXIDE; RAPID REDUCTION; REDUCING SYSTEMS; REFLUXING; ROOM TEMPERATURE; STYRENE OXIDE;

AMIDES; BENZENE; CARBONYLATION; CYANIDES; ESTERS; RESINS; STYRENE; SULFUR; SULFUR COMPOUNDS;

METHANOL;

EID: 0000180963     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.70.1101     Document Type: Article

References (29)

1. N. G. Gaylord, "Reduction with Complex Metal Hydrides", Interscience Publishers, Inc., New York (1956).
2. B. Ganem and J. O. Osby, Chem. Rev., 86, 763 (1986).
3. A. Nose and T. Kudo, Chem. Pharm. Bull., 29, 1159 (1981);
4. J. O. Osby and B. Ganem, Tetrahedron Lett., 26, 6413 (1985);
5. J. C. Sarma and R. P. Sharma, Chem. Ind. (London), 1987, 764.
6. J. Ipaktschi, Chem. Ber., 117, 856 (1984).
7. T. Sato and S. Suzuki, Tetrahedron Lett., 1969, 4555.
8. Y. He, H. Zhao, X. Pan, and S. Wang, Synth. Commun., 19, 3047 (1989).
9. S. Yoo and S. Lee, Synlett, 1990, 419.
10. S. Kano, Y. Tanaka, E. Sugino, and S. Hibino, Synthesis, 1980, 695.
11. S. W. Chaikin and W. G. Brown, J. Am. Chem. Soc, 71, 122 (1949).
12. K. Soai, S. Yokoyama, and A. Ookawa, Synthesis, 1987, 48.
13. 4 decomposes completely in 5 min in methanol, whereas BER decomposes ca. 45% in 1.0 h and slowly thereafter, both in the presence of 0.02 molar amount of nickel boride.
14. N. M. Yoon and J. Choi, Synlett, 1993, 135.
15. N. M. Yoon, J. Choi, and Y. S. Shon, Synth. Commun., 23, 3047 (1993).
16. N. M. Yoon, J. Choi, and H. J. Lee, Bull. Korean Chem. Soc., 14, 543 (1993);
17. N. M. Yoon, H. J. Lee, J. H. Ahn, and J. Choi, J. Org. Chem., 59, 4687 (1994).
18. T. B. Sim and N. M. Yoon, Synlett, 1995, 726.
19. 4, these ratios were reported to be 31/69 and 14/86 respectively: H. C. Brown and J. Muzzio, J. Am. Chem. Soc, 88, 2811 (1966).
20. N. M. Yoon and T. B. Sim, Bull. Korean Chem. Soc., 14, 749 (1993).
21. M. Narisada, I. Horibe, F. Watanabe, and K. Takeda, J. Org. Chem., 54, 5308 (1989).
22. B. Meunier, J. Organomet. Chem., 204, 345 (1981).
23. P. Caubere, Angew. Chem., Int. Ed. Engl., 22, 599 (1983).
24. S. Mitsui, S. Imaizumi, M. Hissashige, and Y. Sugi, Tetrahedron, 29, 4093 (1973).
25. J. L. Fry and T. J. Mraz, Tetrahedron Lett., 1979, 849.
26. G. W. Kabalka, P. P. Wadgaonkar, and N. Chatla, Synth. Commun., 20, 293 (1990).
27. J. Choi and N. M. Yoon, Synthesis, 1996, 597.
28. T. B. Sim, J. H. Ahn, and N. M. Yoon, Synthesis, 1996, 324.
29. J. Choi, J. H. Ahn, and N. M. Yoon, J. Org. Chem., 59, 3490 (1994).