SmI2-mediated elimination reaction of trichloromethyl carbinols: A facile method to synthesize vinyl dichlorides

Tetrahedron Letters

Volumn 44, Issue 52, 2003, Pages 9349-9351

  Li, Jian ^a   Xu, Xiaoliang ^a   Zhang, Yongmin ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Elimination; Samarium diiodide; Trichloromethyl carbinol; Vinyl dichloride

Indexed keywords

CHLORIDE; METHANOL DERIVATIVE; SAMARIUM DIIODIDE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ELIMINATION REACTION; SYNTHESIS;

EID: 0345603775     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.085     Document Type: Article

References (31)

1. Ramirej F., Desai N.B., McKelvie N.J. J. Am. Chem. Soc. 84:1962;1745-1747.
2. Corey E.J., Fuchs P.L. Tetrahedron Lett. 13:1972;3769-3772.
3. Wang Z., Campagna S., Yang K., Xu G., Pierce M.E., Fourtunak J.M., Confalone P.N. J. Org. Chem. 65:2000;1889-1891.
4. Tanaka H., Yamashita S., Yamamoue M., Torii S. J. Org. Chem. 54:1989;444-450.
5. Speziale A.J., Ratts K.W. J. Am. Chem. Soc. 84:1962;854-859.
6. Corey E.J., Fuchs P.L. Tetrahedron Lett. 13:1972;3769-3772.
7. Bandzouzi A., Lakhrissi M., Chapleur Y. J. Chem. Soc., Perkin Trans. 1. 1992;1471-1473.
8. Chaplerur Y. J. Chem. Soc., Chem. Commun. 1984;449-450.
9. Wang Z., Campagna S., Xu G., Pierce M.E., Fortunak J.M., Confalone P.N. Tetrahedron Lett. 41:2000;4007-4009.
10. Calvet F., Mejuto M.N. J. Chem. Soc. 1936;554-556.
11. Kiehlmann E., Bianchi R.J., Reeve W. Can. J. Chem. 47:1969;1521-1527.
12. Gajewski R.P., Jackson J.L., Jones N.D., Swartzendruber J.K., Deeter J.B. J. Org. Chem. 54:1989;3311-3317.
13. Wolf R., Steckhan E. J. Chem. Soc. 1986;733-740.
14. Bitter I., Toke L., Bende Z., Ádám É.K., Soós R. Tetrahedron. 40:1984;4501-4506.
15. Ranu B.C., Samanta S., Das A. Tetrahedron Lett. 43:2002;5993-5995.
16. Lavielle G., Combret J.-C., Villieras J. Bull. Soc. Chim. Fr. 1971;2047-2053.
17. Girard P., Namy J.L., Kagan H.B. J. Am. Chem. Soc. 102:1980;2693-2698.
18. Krief A., Laval A.M. Chem. Rev. 99:1999;745-777.
19. Molander G.A. Acc. Chem. Res. 31:1998;603-609.
20. Molander G.A., Harris C.R. Tetrahedron. 54:1998;3321-3354.
21. Molander G.A., Harris C.R. Chem. Rev. 96:1996;307-338.
22. Molander G.A. Chem. Rev. 92:1992;29-68.
23. Curran D.P., Fevig T.L., Jasperse C.P., Totleben M.J. Synlett. 1992;943-961.
24. For examples: (a) Concellon, J. M.; Bernad, P. J.; Pére- Andrés, J. A. Angew. Chem., Int. Ed. 1999, 38, 2384-2386; (b) Concellon, J. M.; Bernad, P. J.; Pére-Andrés, J. A.; Rodríguez-Solla, H. Angew. Chem., Int. Ed. 2000, 39, 2773-2775; (c) Concellon, J. M.; Huerta, M. Tetrahedron Lett. 2003, 44, 1931-1934; (d) Concellon, J. M.; Bardales, E. Org. Lett. 2002, 4, 189-191; (e) Concellon, J. M.; Bernad, P. J.; Bardales, E. Org. Lett. 2001, 3, 937-939.
25. For examples: (a) Concellon, J. M.; Bernad, P. J.; Pére- Andrés, J. A. Angew. Chem., Int. Ed. 1999, 38, 2384-2386; (b) Concellon, J. M.; Bernad, P. J.; Pére-Andrés, J. A.; Rodríguez-Solla, H. Angew. Chem., Int. Ed. 2000, 39, 2773-2775; (c) Concellon, J. M.; Huerta, M. Tetrahedron Lett. 2003, 44, 1931-1934; (d) Concellon, J. M.; Bardales, E. Org. Lett. 2002, 4, 189-191; (e) Concellon, J. M.; Bernad, P. J.; Bardales, E. Org. Lett. 2001, 3, 937-939.
26. For examples: (a) Concellon, J. M.; Bernad, P. J.; Pére- Andrés, J. A. Angew. Chem., Int. Ed. 1999, 38, 2384-2386; (b) Concellon, J. M.; Bernad, P. J.; Pére-Andrés, J. A.; Rodríguez-Solla, H. Angew. Chem., Int. Ed. 2000, 39, 2773-2775; (c) Concellon, J. M.; Huerta, M. Tetrahedron Lett. 2003, 44, 1931-1934; (d) Concellon, J. M.; Bardales, E. Org. Lett. 2002, 4, 189-191; (e) Concellon, J. M.; Bernad, P. J.; Bardales, E. Org. Lett. 2001, 3, 937-939.
27. For examples: (a) Concellon, J. M.; Bernad, P. J.; Pére- Andrés, J. A. Angew. Chem., Int. Ed. 1999, 38, 2384-2386; (b) Concellon, J. M.; Bernad, P. J.; Pére-Andrés, J. A.; Rodríguez-Solla, H. Angew. Chem., Int. Ed. 2000, 39, 2773-2775; (c) Concellon, J. M.; Huerta, M. Tetrahedron Lett. 2003, 44, 1931-1934; (d) Concellon, J. M.; Bardales, E. Org. Lett. 2002, 4, 189-191; (e) Concellon, J. M.; Bernad, P. J.; Bardales, E. Org. Lett. 2001, 3, 937-939.
28. For examples: (a) Concellon, J. M.; Bernad, P. J.; Pére- Andrés, J. A. Angew. Chem., Int. Ed. 1999, 38, 2384-2386; (b) Concellon, J. M.; Bernad, P. J.; Pére-Andrés, J. A.; Rodríguez-Solla, H. Angew. Chem., Int. Ed. 2000, 39, 2773-2775; (c) Concellon, J. M.; Huerta, M. Tetrahedron Lett. 2003, 44, 1931-1934; (d) Concellon, J. M.; Bardales, E. Org. Lett. 2002, 4, 189-191; (e) Concellon, J. M.; Bernad, P. J.; Bardales, E. Org. Lett. 2001, 3, 937-939.
29. Corey E.J., Link J.O., Shao Y. Tetrahedron Lett. 33:1992;3435-3438.
30. Aggarwal V.A., Mereu A. J. Org. Chem. 65:2000;7211-7212.
31. abstract