A new and efficient electrosynthesis of 2-substituted 1,1- cylopropanediylbis(phosphonates)

Synthesis

Volumn , Issue 11, 1999, Pages 1903-1906

  Goumain, Sophie ^a   Jubault, Philippe ^a   Feasson, Christian ^a   Collignon, Noël ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

Cyclizations; Cyclopropanation; Cyclopropanes; Electrolysis; Michael acceptors; Phosphorus; Tetraethyl dichloromethylbis(phosphonate)

Indexed keywords

CYCLOPROPANE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; ELECTROCHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0032731302     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3610     Document Type: Article

References (27)

1. (a) Salaün, J; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
2. (b) Kuo, M. S.; Zielinski, R. J.; Ciadella, J. I.; Marschke, C. K.; Dupuis, M. J.; Li, G. P.; Kloosterman, D. A.; Spilman, C. H.; Marshall, V. P. J. Am. Chem. Soc. 1995, 117, 10629.
3. (c) Gerwick, W. H.; Proteau, P. J.; Nagle, D. G.; Hamel, E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994, 59, 1243.
4. (a) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
5. (b) de Meijere, A.; Wessjohann, L. Synlett 1990, 20.
6. (a) Stammer, C. H. Tetrahedron 1990, 46, 2231.
7. (b) Burgess, K.; Ho, K.-K.; Pettitt, B. M. J. Am. Chem. Soc. 1995, 117, 54.
8. (a) He, M.; Dowd, P. J. Am. Chem. Soc. 1996, 118, 711.
9. (b) Mattalia, J.-M.; Chanon, M.; Stirling, C. J. M. J. Org. Chem. 1996, 61, 1153.
10. (c) Suckling, C. J. Angew. Chem. 1988, 100, 555; Angew. Chem., Int. Ed. Engl. 1988, 27, 537.
11. (c) Suckling, C. J. Angew. Chem. 1988, 100, 555; Angew. Chem., Int. Ed. Engl. 1988, 27, 537.
12. (a) The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley: New York, 1995; Vol. 2.
13. (b) Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Ed.; Pergamon: Oxford, 1991, Vol. 4, pp 951-1067.
14. Rodan, G.; Fleisch, H. A. J. Clin. Invest. 1996, 97, 2692.
15. Sato, M.; Grese, T. A.; Dodge, J. A.; Bryant, H. U.; Turner, C. H. J. Med. Chem. 1999, 42, 1.
16. Reginster, J. Y. L.; Halkin, V.; Gosset, C.; Deroisy, R. Drugs Today 1997, 33, 563.
17. Hutchinson, D. W.; Thornton, D. M. Synthesis 1990, 135.
18. Chenye, Y.; Chaozhong, L.; Yixiang, D. Synthesis 1991, 854.
19. Villemin, D.; Thibault-Starzyk, F; Hachemi, M. Synth. Comm. 1994, 24, 1425.
20. Yamazaki, S.; Takada, T.; Imanishi, T.; Moriguchi, Y.; Yamabe, S. J. Org. Chem. 1998, 63, 5919.
21. Simonet, J.; Le Guillanton, G. Bull. Soc. Chim. Fr. 1986, 2, 221.
22. Niyazymbetov, M. E.; Evans, D. H. Tetrahedron 1993, 49, 9627.
23. Utley, J. Chem. Soc. Rev. 1997, 26, 157.
24. Jubault, P.; Goumain, S.; Feasson, C.; Collignon, N. Tetrahedron 1998, 54, 14767.
25. Goumain, S.; Jubault, P.; Feasson, C.; Collignon, N. Synthesis 1999, 981.
26. Devaud, M.; Azzouzi, F.; Tue Bi, B. J. Chem. Res. (M) 1991, 1052.
27. Mc Kenna, C. E.; Khawli, L. A. J. Org. Chem. 1986, 51, 5467.