Alternative and mild procedures for the removal of organotin residues from reaction mixtures

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2123-2126

  Renaud, Philippe ^a   Lacôte, Emmanuel ^a   Quaranta, Laura ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; HALIDE; ORGANOTIN COMPOUND; SILICA GEL; SODIUM HYDROXIDE; TRIBUTYLTIN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; EXTRACTION; HYDROLYSIS; METAL BINDING; SYNTHESIS;

EID: 0032499036     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00066-5     Document Type: Article

References (18)

1. 1. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1988.
2. (b) Motherwell, W. B. ; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992.
3. (c) Curran, D. P. ; Porter, N. A. ; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996.
4. 2. Neumann, W. P. Synthesis 1987, 665-683.
5. 3. (a) Light, J. ; Breslow, R. Tetrahedron Lett. 1990, 31, 2957-2958.
6. (b) Gerlach, M. ; Jördens, F. ; Kuhn, H. ; Neumann, W. P. ; Petersheim, M. J. Org. Chem. 1991, 56, 5971-5972.
7. (c) Rai, R. ; Collum, D. B. Tetrahedron Lett. 1994, 35, 6221-6224.
8. (d) Fouquet, E. ; Pereyre, M. ; Roulet, T. J. Chem. Soc., Chem. Commun. 1995, 2387-2388.
9. (e) Clive, D. L. J. ; Yang, W. J. Org. Chem. 1995, 60, 2607-2609.
10. (f) Curran, D. P. ; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531-2532.
11. 4. Berge, J. M. ; Roberts, S. M. Synthesis 1979, 471-472.
12. 5. Curran, D. P. ; Chang, C. J. Org. Chem. 1989, 3140-3157.
13. 6. Leibner, J. E.; Jacobus, J. J. Org. Chem. 1979, 44, 449-450.
14. 7. Crich, D.; Sun, S. J. Org. Chem. 1996, 61, 7200-7201.
15. 8. Using this approach, we observed a complete degradation of α-alkylated β-ketosulfoxides presumably via the thermal elimination of a sulfenic acid.
16. 9. Renaud, P. Chimia 1997, 51, 236-238.
17. 10. Neumann, W. P. Liebigs Ann. Chem. 1962, 653, 157-163.
18. 11. For a discusssion of the hydrolysis products of organotin halides, see chapter 10 in: Davies, A. G. Organotin Chemistry; VCH: Weinheim, 1997.