An efficient synthesis of dinitrile derivatives by the reaction of oxime esters or acid anhydrides with cyanotrimethylsilane catalyzed by La(O(i)PR)3

Journal of Organic Chemistry

Volumn 65, Issue 19, 2000, Pages 6209-6212

  Fujii, Akiko ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; LANTHANIDE; NITRILE; OXIME; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034703398     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0055281     Document Type: Article

References (29)

1. (a) March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; pp 964-965.
2. (b) Groutas, W. C.; Felker, D. Synthesis 1980, 861.
3. (a) Matsubara, S.; Kodama, T.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6379.
4. (b) Sasaaman, M. B.; Surya Prakash, G. K.; Olah, G. A. J. Org. Chem. 1990, 55, 2016.
5. (c) Imi, K.; Yanagihara, N.; Utimoto, K. J. Org. Chem. 1987, 52, 1013.
6. (a) Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537.
7. (b) Reetz, M. T.; Drewes, M. W.; Harms, K.; Reif, W. Tetrahedron Lett. 1988, 29, 3295.
8. (c) Vougioukas, A. E.; Kagan, H. B. Tetrahedron Lett. 1987, 28, 5513.
9. (d) Comber, R. N.; Hosmer, C. A.; Brouillette, W. J. J. Org. Chem. 1985, 50, 3627.
10. (e) Greenlee, W. J.; Hangauer, D. G. Tetrahedron Lett. 1983, 24, 4559.
11. (f) Utimoto, K.; Wakabayashi, Y.; Horiie, T.; Inoue, M.; Shishiyama, Y.; Obayashi, M.; Nozaki, H. Tetrahedron 1983, 39, 967.
12. (g) Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37, 3899.
13. (h) Gassman, P. G.; Talley, J. J. Tetrahedron Lett. 1978, 3773.
14. (i) Evans, D. A.; Carroll, G. L.; Truesdale, L. K. J. Org. Chem. 1974, 39, 914.
15. (j) Lidy, W.; Sundermeyer, W. Chem. Ber. 1973, 106, 587.
16. Matsubara, S.; Takai, T.; Utimoto, K. Chem. Lett. 1991, 1447.
17. Hermann, K.; Simchen, G. Synthesis 1979, 204.
18. (a) Yamaguchi, S.; Araki, H.; Hanafusa, T. Chem. Lett. 1985, 685.
19. (b) Lidy, W.; Sundermeyer, W. Tetrahedron Lett. 1973, 14, 1449.
20. (a) Mizuno, M.; Shioiri, T. Tetrahedron Lett. 1998, 39, 9209.
21. (b) Tanaka, M. Tetrahedron Lett. 1980, 21, 2959.
22. Kawasaki, Y.; Fujii, A.; Nakano, Y.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1999, 64, 4214.
23. Tashiro, D.; Kawasaki, Y.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1997, 62, 8141.
24. 5
25. Evans, W. J.; Bloom, I.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1981, 103, 6507.
26. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
27. Yu, Y.; Lin, R.; Zhang, Y. Tetrahedron Lett. 1993, 34, 4547.
28. Hoffman, R. V.; Buntain, G. A. Synthesis 1987, 831.
29. Hertenstein, U.; Huenig, S. Reichelt, H.; Schaller, R. Chem. Ber. 1982, 115, 261.