Sodium amalgam, a useful reducing reagent for formation of amines from azides bearing a variety of functional groups

Chinese Journal of Chemistry

Volumn 23, Issue 12, 2005, Pages 1637-1640

  Lu, Biao ^a   Zhu, Ji Dong ^b   Xie, Xiao An ^a   Ma, Da Wei ^b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Azides; Reduction; Sodium amalgam

Indexed keywords

EID: 30744452479     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.200591637     Document Type: Article

References (20)

1. (a) Marson, C.; Hobson, A. D. In Comprehensive Organic Functional Group Transformations, Ed.: Ley, S. V., Pergammon Elsevier, Oxiford, UK, 1995, p. 297.
2. (b) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 298.
3. Bietschneider, H.; Hormann, H. H. Monatsh 1953, 84, 1021.
4. Boyer, J. H. J. Am. Chem. Soc. 1951, 73, 5865
5. (a) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
6. (b) Vaultier, M.; Konuzi, N.; Carrie, R. Tetrahedron Lett. 1983, 24, 763.
7. Nyffeler, P. T.; Liang, C. H.; Koeller, K. M.; Wong, C. H. J. Am. Chem. Soc. 2002, 124, 5865.
8. (a) Bosch, I.; Costa, A. M.; Martin, M.; Urpi, F.; Vilarrasa, J. Org. Lett. 2000, 2, 397.
9. (b) Ranu, B. C.; Sarkar, A.; Chakraborty, R. J. Org. Chem. 1994, 59, 4114.
10. (c) Alvarez, S. G.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1995, 36, 2567.
11. (d) Salunkhe, A. M.; Brown, H. C. Tetrahedron Lett. 1995, 36, 7987.
12. Goulaouic-Dubois, C.; Hessse, M. Tetrahedron Lett. 1995, 36, 7427.
13. Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 2796.
14. (a) Kami, A.; Laxminarayana, B.; Gayatri, N. L. Tetrahedron Lett. 1997, 38, 6871.
15. (b) Kaml, A.; Rao, N. V.; Laxman, E. Tetrahedron Lett. 1997, 39, 6945.
16. (c) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937.
17. (d) Sridhar, P. R.; Prabhu, K. A.; Chandrasekaran, S. J. Org. Chem. 2003, 68, 5261.
18. Zhu, J.; Ma, D. Angew. Chem., Int. Ed. 2003, 42, 5349.
19. Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis, Vol. 1, John Wiley, New York, 1967, pp. 1030-1033.
20. Zhu, W.; Ma, D. Chem. Commun. 2004, 888.