CeCl3/Sm system induced reductive cleavage of the Se-Se bond in diaryl diselenides: A novel method for the synthesis of β-selenoesters and β-selenonitriles

Journal of the Chinese Chemical Society

Volumn 49, Issue 6, 2002, Pages 1111-1113

  Li, Xue ^a   Zhang, Songlin ^a   Wang, Yulu ^a   Zhang, Yongmin ^b  

^a HENAN NORMAL UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

Arylseleno esters; Arylseleno nitriles; Cerium(III) chloride; Samarium

Indexed keywords

EID: 3042690239     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200200160     Document Type: Article

References (36)

1. Peich, H. T. Acc. Chem. Res. 1979, 12, 22.
2. Kato, S.; Murai, T.; Masura, M. Org. Prep. Proced. Int. 1986, 18, 369.
3. Perrick, L. T. Tetrahedron 1978, 34(8), 1049.
4. Griceo, P. A.; Yokoyama, Y.; Williams, E. J. Org. Chem. 1978, 43, 1283.
5. Kataev, E. G.; Gabdrakhmanav, F. G. Zh. Obshch. Khim. 1967, 37, 772.
6. Miyashita, M.; Yoshikashi, A. Synthesis 1980, 8, 664.
7. Jiang, H.; Zhang, Y. Hecheng Huaxue 1993, 3, 248.
8. Ogawa, A.; Nishiyama, Y.; Kambe, N.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1987, 28, 3271.
9. Imamoto, T. Lanthanides in Organic Synthesis', Academic Press: New York, 1994.
10. (a) Liu, H. J.; Shia, K. S.; Shang, X.; Zhu, B. Y. Tetrahedron 1999, 55, 3803-3830.
11. (b) Alessandrini, S.; Bartoli, G.; Bellucci, M. C.; Dalpozzo, R.; Malavolta, M.; Marcantoni, E.; Sambri, L. J. Org. Chem. 1999, 64, 1986-1992.
12. (c) Ballini, R.; Marcantoni, E.; Perella, S. J. Org. Chem. 1999, 64, 2954-2957.
13. (d) Bartoli, G.; Bosco, M.; Dalpozzo, R.; De Nino, A.; Marcantoni, E.; Sambri, L. J. Org. Chem. 1998, 63, 3745-3747.
14. (e) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem.-Eur. J. 1997, 3, 1941-1950.
15. (f) Bartoli, G.; Marcantoni, E.; Petrini, M.; Sambri, L. Chem.-Eur. J. 1996, 2, 973-979.
16. (g) Bartoli, G.; Marcantoni, E.; Sambri, L.; Tamburini, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2046-2049.
17. Lantens, M.; De Frutos, O.; Stammers, T. Tetrahedron Lett. 1999, 40(48), 8317-8321.
18. (a) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; T. Mita, T.; Hatanaka, Y.; Yokoyama, Y. J. Org. Chem. 1984, 49(21), 3904.
19. (b) Imamoto, T.; Sugiura, Y. J. Organomet. Chem. 1985, 285(1-3), C21.
20. (c) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25(38), 4233.
21. (a) Sakair, N.; Hayashida, M.; Kuzuhara, H. Tetrahedron Lett. 1987, 28, 2871.
22. (b) Kato, N.; Kataoka, H.; Ohbuchi, S.; Tanaka, S.; Takeshita, H. J. Chem. Soc., Chem. Commun. 1988, 354.
23. (c) Fleming, I.; Higgins, D. Tetrahedron Lett. 1989, 30, 5777.
24. (d) Danishefsky, S. J.; De Ninno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929.
25. (e) DeShong, P.; Waltermire, R. E.; Ammon, H. L. J. Am. Chem. Soc. 1988, 110, 1901.
26. (f) Abelman, M. M.; Overman, L. E.; Tran, V. D. J. Am. Chem. Soc. 1990, 112, 6959.
27. (a) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
28. (b) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573.
29. (c) Molander, G. A. Chem. Rev. 1992, 92, 29.
30. (d) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
31. Zhou, L.; Zhang, Y. Synth. Commun. 1999, 29(3), 533-540.
32. (a) Zhang, S.; Zhang, Y. Org. Prep. Proced. Int. 1999, 31(4), 450-453.
33. (b) Zhang, S.; Zhang, Y. Synth. Commun. 2000, 30(2), 285-292.
34. Wang, L.; Zhang, Y. Heteroatom Chemistry 1999, 10(3), 203-208.
35. Chen, R.; Zhang, Y. Synth. Commun. 2000, 30(7), 1331-1336.
36. Zhang, S.; Zhang, Y. Chinese Chem. Lett. 1998, 9, 885.