A novel debromination of vic-dibromides to alkenes with InCl3(cat.)/Sm system in aqueous media
Min Wang
Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, China
Search for more papers by this authorLei Wang
Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, China
State Key Laboratory of Organometallic Chemistry. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorPin-Hua Li
Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, China
Search for more papers by this authorJin-Can Yan
Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, China
Search for more papers by this authorMin Wang
Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, China
Search for more papers by this authorLei Wang
Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, China
State Key Laboratory of Organometallic Chemistry. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorPin-Hua Li
Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, China
Search for more papers by this authorJin-Can Yan
Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, China
Search for more papers by this authorAbstract
A novel debromination of vic-dibromides to alkenes with InCl3(cat.)/Sm system in aqueous media has been developed. The reaction gives the E-isomers with excellent yields.
References
- 1 Schlosser, M. Methoden der Oragnishchen Chemie. 4th ed., Ed.: E. Muller, Vol. V/1b, Georg Thieme Verlag, Stuttgart, 1972. p. 202.
- 2 Adam, W.; Arce, J. J. Org. Chem 1972, 37, 507.
- 3 Schubert W. M.; Rabinovitch, B. S.; Larson, N. R.; Sims, V. A. J. Am. Chem Soc. 1952, 74, 4590.
- 4 Buckles, R. E.; Bader, J. M.; Thurmaier, R. J. J. Org. Chem 1962, 27, 4532.
- 5 Prince, M.; Bremer, B. W.; Brenner, W. J. Org. Chem 1966, 31, 4292.
- 6 King, J. F.; Pews, R. C. Can. J. Chem 1964, 42, 1294.
- 7 Fukunaga, K.; Yamaguchi, H. Synthesis 1981, 879.
- 8 Olah, G. A.; Prakash, G. K. S. Synthesis 1976, 607.
- 9 Halpern, J.; Maher, J. P. J. Am. Chem Soc. 1965, 87, 5361.
- 10 Nozaki, H.; Shirafuji, T.; Yamamoto, Y. Tetrahedron 1969, 25, 3461.
- 11 Kray, W. C.; Castro, C. E. J. Am Chem Soc. 1964, 86, 4603.
- 12 Strunk, R. J.; DiGiacomo, P. M.; Aso, K.; Kuivila, H. G. J. Am Chem. Soc. 1970, 92, 2849.
- 13(a) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741. (b) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media, Wiley, New York, 1997. (c) Lindstrom, U. M. Chem Rev. 2002, 102, 2751.
- 14(a) Li, C. J. Chem Rev. 1993, 93, 2023. (b) Li, C. J. Tetrahedron 1996, 52, 5643. (c) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (d) Chauhan, K. K.; Frost, C. G. J. Chem Soc., Perkin Trans. 1 2000, 3015. (e) Chtas, P. Synlett 1995, 1087.
- 15(a) Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017. (b) Chan, T. H.; Li, C. J. J. Chem. Soc., Chem Commun 1992, 747. (c) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181. (d) Wang, L.; Sun, X.; Bang, Y. Synth Commun., 1998, 32, 3263.
- 16(a) Ranu, B. C.; Guchhait, S. K.; Sarkar, A. J. Chem Soc., Chem Commun. 1998, 2113. (b) Moody, C. J.; Pitts, M. R. Synlett 1998, 1028. (c) Moody, C. J.; Pitts, M. R. Synlett 1998, 1029. (d) Ranu, B. C.; Dutta, P.; Sarkar, A. J. Chem Soc., Perkin Trans. 1 1999, 1139. (e) Reddy, G. V.; Rao, G. V.; Iyenger, D. S. Tetrahedron Lett. 1999, 40, 3937. (f) Chae, H.; Cho, S.; Keum, G.; Kang, S. B.; Pae, A. N.; Kim, Y. Tetrahedron Lett. 2000, 41, 3899. (g) Ranu, B. C.; Samanta, S.; Guchhait, S. K. J. Org. Chem. 2001, 66, 4102.
- 17 Kornblum, N.; Boyd, S. D.; Pinnick, H. W.; Smith, R. G. J. Am Chem Soc. 1971, 93, 4316.
- 18 Mathai, I. M.; Schung, K.; Miller, S. I. J. Org. Chem 1970, 35, 1733.
- 19 Kray, W. C.; Castro, C. E. J. Am Chem Soc. 1964, 86, 4603.
- 20 Corson, B. B.; Ipatieff, V. N. Org. Synth Collect. Vol. II 1950, 152.
- 21 Marvel, C. S.; King, W. B. Org. Synth Collect. Vol. I 1956, 252.
- 22 Buckingham, J. Dictionary of Organic Compounds, Chapman and Hall, New York, 5th ed., 1982.
- 23 Effenberger, F.; Bessey, E. Chem. Ber. 1980, 113, 2100.
- 24 Chenevert, R.; Desjardins, M. Can. J. Chem 1994, 72, 2312.
- 25 Arvidsson, L. E.; Johansson, A. M.; Hacksell, U.; Nilsson, J. L.; Svensson, K.; Hjorth, S.; Magnusson, T.; Carlsson, A.; Lindberg, P.; Andersson, B. J. Med Chem. 1988, 31, 92.
