Novel reductive dimerization cyclization of 1,1-dicyanoalkenes mediated by zinc in aqueous media

Synthetic Communications

Volumn 28, Issue 17, 1998, Pages 3269-3277

  Wang, Lei ^a   Zhang, Yongmin ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DICYANOALKENE; ALKENE; CYCLOPENTENE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CYCLIZATION; DIMERIZATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE;

EID: 0031902311     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004432     Document Type: Article

References (29)

1. (a) Huffman, J. W. and Charles, J. T. J. Am. Chem. Soc. 1968, 90, 6486.
2. (b) House, H. O., McDaniel, W. C., Sieloff, R. F. and Vanderveer, D. J. Org. Chem. 1979, 43, 4316.
3. Botteron, D. G. and Wood, G. J. Org. Chem. 1965, 30, 3871.
4. Schreibmann, A. A. P. Tetrahedron Lett. 1970, 4271.
5. (e) Corey, E. J. and Carney, R. L. J. Am. Chem. Soc. 1971, 93, 7318.
6. (f) FÜrstner, A., Csuk, R., Rohrer, C. and Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729.
7. (a) Bloomfield, J. J., Owsley, D. C. and Nelke, J. M. Org. React. 1976, 23, 259.
8. (b) Gassman, P. G. and Creary, X. J. Chem. Soc., Chem. Commun. 1972, 1214.
9. RÜhlman, K. Synthesis 1971, 236.
10. Bartezko, R., Gleiter, R., Muthard, J. L. and Paquette, L. A. J. Am. Chem. Soc. 1978, 100, 5589
11. (a) Eisch, J. J., Kaska, D. D. and Peterson, C. J. J. Org. Chem. 1966, 31, 453.
12. (b) Smith, J. G. and Ho, I. J. Org. Chem. 1972, 37, 653.
13. Mehrotra, K. N. and Giri, B. P. Synthesis 1977, 489.
14. (a) Inanaga, J., Handa, Y., Tabuchi, T., Otsubo, K., Yamaguchi, M. and Hanamoto, T. Tetrahedron Lett. 1991, 32, 6557
15. (b) Kanemasa, S., Yamamoto, H. and Kobayashi, S. Tetrahedron Lett. 1996, 37, 8505.
16. (a) Chan, T. H. and Isaac, M. B. Pure Appl Chem. 1996, 68, 919.
17. (b) Yamamoto, Y. and Asao, N. Chem. Rev. 1993, 93, 2207
18. Li, C. J. Chem. Rev. 1993, 93, 2023.
19. Lubineau, A., Augé, J. and Queneau, Y. Synthesis 1994, 741
20. (a) Paquette, L. A. and Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931.
21. (b) Paquette, L. A and Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917.
22. Li, C. J., Chen, D. L., Lu, Y. Q., Haberman, J. X and Magqe, J. T J. Am. Chem. Soc. 1996, 118, 4216.
23. (a) Petrier, C. and Luche, J. L. J. Org. Chem 1985, 50, 910.
24. (b) Petrier, C., Einhorn, J. and Luche, J. L. Tetrahedron Lett. 7985, 26, 1449.
25. Einhorn, J. and Luche, J. L. J. Organomet. Chem. 1987, 322, 177.
26. Wilson, S. R. and Guazzaroni, M E. J. Org. Chem. 1989, 54, 3087.
27. (e) Luche, J. L. and Damiano, J. C. J. Am. Chem. Soc. 1980, 102, 7926.
28. (a) Chan, T. H., Li, C. J. and Wei, Z. J. J. Chem. Soc., Chem. Commun. 1990, 505.
29. (b) Marton, D., Stivanello, D. and Tagliavini, G J. Org. Chem. 1996, 61, 2731.