Dry reaction of diethyl cyanomethylphosphonate and tetraethyl methylenediphosphonate with benzaldehyde on solid bases

Phosphorus, Sulfur and Silicon and Related Elements

Volumn 113, Issue 1-4, 1996, Pages 131-136

  Hachemi, Messaoud ^a   Puciova Sebova, Monika ^b   Toma, Stefan ^b   Villemin, Didier ^a  

^a UNIVERSITÉ DE CAEN   (France)

^b Physics and Informatics   (Slovakia)

Author keywords

Basicity; Horner; Knoevenagel; Phosphonate; Solid bases

Indexed keywords

EID: 0042785492     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426509608046384     Document Type: Article

References (27)

1. J. Villieras, M. Rambaud and B. Kirschleger, Phosphorus and Sulfur, 14, 385 (1983); J. Villieras and M. Rambaud, Synthesis, 924 (1982) and 300 (1983); J. Villieras, M. Rambaud and M. Graff, Tetrahedron Lett., 26, 53 (1985).
2. J. Villieras, M. Rambaud and B. Kirschleger, Phosphorus and Sulfur, 14, 385 (1983); J. Villieras and M. Rambaud, Synthesis, 924 (1982) and 300 (1983); J. Villieras, M. Rambaud and M. Graff, Tetrahedron Lett., 26, 53 (1985).
3. J. Villieras, M. Rambaud and B. Kirschleger, Phosphorus and Sulfur, 14, 385 (1983); J. Villieras and M. Rambaud, Synthesis, 924 (1982) and 300 (1983); J. Villieras, M. Rambaud and M. Graff, Tetrahedron Lett., 26, 53 (1985).
4. J. Villieras, M. Rambaud and B. Kirschleger, Phosphorus and Sulfur, 14, 385 (1983); J. Villieras and M. Rambaud, Synthesis, 924 (1982) and 300 (1983); J. Villieras, M. Rambaud and M. Graff, Tetrahedron Lett., 26, 53 (1985).
5. F. Texier-Boullet and A. Foucaud, Synthesis, 884 (1979); W. C. Still and C. Gennari, Tetrahedron Lett., 4405 (1983).
6. F. Texier-Boullet and A. Foucaud, Synthesis, 884 (1979); W. C. Still and C. Gennari, Tetrahedron Lett., 4405 (1983).
7. F. Texier-Boullet and A. Foucaud, Tetrahedron Lett., 21, 2161 (1980).
8. F. Texier-Boullet and A. Foucaud, Tetrahedron Lett., 23, 4927 (1982).
9. Texier-Boullet, D. Villemin, M. Ricard, H. Moison and A. Foucaud, Tetrahedron, 41, 1259 (1985); D. Villemin, Chem. Ind., 166 (1985) and 69 (1986).
10. Texier-Boullet, D. Villemin, M. Ricard, H. Moison and A. Foucaud, Tetrahedron, 41, 1259 (1985); D. Villemin, Chem. Ind., 166 (1985) and 69 (1986).
11. Texier-Boullet, D. Villemin, M. Ricard, H. Moison and A. Foucaud, Tetrahedron, 41, 1259 (1985); D. Villemin, Chem. Ind., 166 (1985) and 69 (1986).
12. J. V. Sinesterra, Z. Mouloungui, M. Delmas and A. Gaset, Synthesis, 1097 (1985).
13. J. V. Sinesterra, J. Barrios, Z. Mouloungui, M. Delmas and A. Gaset, Bull. Soc. Ch. Belge, 100, 257 (1991).
14. H. Moison, F. Texier-Boullet and A. Foucaud, Tetrahedron, 43, 537 (1987).
15. J. I. G. Cardogan, "Organophosphorus Reagents in Organic Synthesis," Academic Press, London, New York, 1979; A. Johnson, "Ylid Chemistry," Academic Press, New York, 1966; W. S. Wadsworth, Jr., Organic Reaction, 25, 73 (1978).
16. J. I. G. Cardogan, "Organophosphorus Reagents in Organic Synthesis," Academic Press, London, New York, 1979; A. Johnson, "Ylid Chemistry," Academic Press, New York, 1966; W. S. Wadsworth, Jr., Organic Reaction, 25, 73 (1978).
17. J. I. G. Cardogan, "Organophosphorus Reagents in Organic Synthesis," Academic Press, London, New York, 1979; A. Johnson, "Ylid Chemistry," Academic Press, New York, 1966; W. S. Wadsworth, Jr., Organic Reaction, 25, 73 (1978).
18. A. Radial and J. Seyden-Penne, Tetrahedron Lett., 1733 (1974).
19. W. Lehnert, Tetrahedron, 30, 301 (1974).
20. pKa estimated with CAMEO software (error ΔpKa ± 3): T. D. Salatin and W. L. Jorgensen, J. Org. Chem., 45, 2043 (1980).
21. The pKa of (2) was not available and was estimated by comparison with the pKa of diethyl phosphonoacetate (12.2) and the pKa of ethylcyanoacetate (9.0): M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. Roush and T. Sakai, Tetrahedron Lett., 25, 2183 (1984); R. G. Pearson and R. L. Dillon, J. Amer. Chem. Soc., 75, 2439 (1953).
22. The pKa of (2) was not available and was estimated by comparison with the pKa of diethyl phosphonoacetate (12.2) and the pKa of ethylcyanoacetate (9.0): M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. Roush and T. Sakai, Tetrahedron Lett., 25, 2183 (1984); R. G. Pearson and R. L. Dillon, J. Amer. Chem. Soc., 75, 2439 (1953).
23. G. Bram, A. Loupy and D. Villemin, in "Solid Supports and Catalysts in Organic Synthesis," Chap. 12, pp. 302-326, K. Smith ed., Ellis Horwood and Prentice Hall, 1992.
24. J. H. Clark, A. J. Hyde and D. K. Smith, J. Chem. Soc., Chem. Commun., 791 (1986); J. Ichihara, T. Matsuo, T. Hanafusa and T. Ando, J. Chem. Soc., Chem. Commun., 793 (1986).
25. J. H. Clark, A. J. Hyde and D. K. Smith, J. Chem. Soc., Chem. Commun., 791 (1986); J. Ichihara, T. Matsuo, T. Hanafusa and T. Ando, J. Chem. Soc., Chem. Commun., 793 (1986).
26. D. Villemin and M. Hachemi, React. Kin. Cat. Lett., 53, 147 (1994).
27. M. Rambaud, A. Vecchio and J. Villieras, Synth. Commun., 14, 833 (1984).