Electrophilicity parameters for benzylidenemalononitriles

Journal of Organic Chemistry

Volumn 68, Issue 18, 2003, Pages 6880-6886

  Lemek, Tadeusz ^a   Mayr, Herbert ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILICITY;

NEGATIVE IONS; REACTION KINETICS;

ORGANIC COMPOUNDS;

ACETOACETIC ACID ETHYL ESTER; ACETYLACETONE; AMINE; ANION; BENZYLIDENEMALONONITRILE; CARBANION; DIMETHYL SULFOXIDE; ENAMINE; ETHANE; ETHYL CYANOACETATE; HYDROXIDE; MALONIC ACID; MALONIC ACID DIETHYL ESTER; MALONONITRILE; NITROETHANE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; ELECTRICAL PARAMETERS; ELECTROPHILICITY PARAMETER; QUANTITATIVE ANALYSIS;

EID: 0041336843     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0344182     Document Type: Article

References (69)

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6. For reactions of carbocations with π-nucleophiles, see: Mayr, H.; Gotta, M. F.; Bug, T.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R. ; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500-9512.
7. For reactions of carbocations with hydride donors, see: (a) Funke, M. A. ; Mayr, H. Chem. Eur. J. 1997, 3, 1214-1222. (b) Mayr, H.; Lang, G.; Ofial, A. R. J. Am. Chem. Soc. 2002, 124, 4076-4083.
8. For reactions of carbocations with hydride donors, see: (a) Funke, M. A. ; Mayr, H. Chem. Eur. J. 1997, 3, 1214-1222. (b) Mayr, H.; Lang, G.; Ofial, A. R. J. Am. Chem. Soc. 2002, 124, 4076-4083.
9. For reactions of carbocations with n-nucleophiles, see: Minegishi, S.; Mayr, H. J. Am. Chem. Soc. 2003, 125, 286-295.
10. Richard, J. P.; Toteva, M. M.; Crugeiras, J. J. Am. Chem. Soc. 2000, 122, 1664-1674.
11. Lucius, R.; Mayr, H. Angew. Chem. 2000, 112, 2086-2089; Angew. Chem., Int. Ed. 2000, 39, 1995-1997.
12. Lucius, R.; Mayr, H. Angew. Chem. 2000, 112, 2086-2089; Angew. Chem., Int. Ed. 2000, 39, 1995-1997.
13. Lucius, R.; Loos, R.; Mayr, H. Angew. Chem. 2002, 114, 97-102; Angew. Chem., Int. Ed. 2002, 41, 91-95. The N and s parameters for 2a change to N = 21.54 and s = 0.62 when rate constants for the reactions of 2a with further quinone methides are included in the correlation. See Supporting Information.
14. Lucius, R.; Loos, R.; Mayr, H. Angew. Chem. 2002, 114, 97-102; Angew. Chem., Int. Ed. 2002, 41, 91-95. The N and s parameters for 2a change to N = 21.54 and s = 0.62 when rate constants for the reactions of 2a with further quinone methides are included in the correlation. See Supporting Information.
15. For Michael adducts or retro-Michael addition products from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Goncharenko, M. P.; Sharanin, Yu. A.; Turov, A. V. Zh. Org. Khim. 1993, 29, 1610-1618; Russ. J. Org. Chem. 1993, 29, 1341-1347. (b) Michaud, D.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1997, 38, 7563-7564. (c) El-Shafei, A. K.; El-Sayed, A. M.; Sultan, A.; Abdel-Ghany, H. Gazz. Chim. Ital. 1990, 120, 197-201. (d) Ma̧kosza, M.; Kwast, A. Tetrahedron 1991, 47, 5001-5018. (e) Martín, N.; Quinteiro, M.; Seoane, C.; Soto, J. L. Liebigs Ann. Chem. 1990, 101-104. (f) Bogdanowicz-Szwed, K.; Czarny, A. J. Prakt. Chem. 1993, 335, 279-282. (g) Elagamey, A. G. A.; Abdel-Ghany, A.; Sofan, M. A.; Kandeel, Z. E.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1987, 52, 1561-1565. (h) Sadek, K. U.; Hafez, E. A. A.; Mourad Abo-Elfetouh, E.; Elnagdi, M. H. Z. Naturforsch. B 1984, 39, 824-828. (i) Negm, A. M.; Abd El-Aal, F. A. E.-M.; Hafez, E. A.; Elnagdi, M. H.; Mostafa, J. M. N. Phosphorus, Sulfur, Silicon 1995, 106, 1-7.
16. For Michael adducts or retro-Michael addition products from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Goncharenko, M. P.; Sharanin, Yu. A.; Turov, A. V. Zh. Org. Khim. 1993, 29, 1610-1618; Russ. J. Org. Chem. 1993, 29, 1341-1347. (b) Michaud, D.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1997, 38, 7563-7564. (c) El-Shafei, A. K.; El-Sayed, A. M.; Sultan, A.; Abdel-Ghany, H. Gazz. Chim. Ital. 1990, 120, 197-201. (d) Ma̧kosza, M.; Kwast, A. Tetrahedron 1991, 47, 5001-5018. (e) Martín, N.; Quinteiro, M.; Seoane, C.; Soto, J. L. Liebigs Ann. Chem. 1990, 101-104. (f) Bogdanowicz-Szwed, K.; Czarny, A. J. Prakt. Chem. 1993, 335, 279-282. (g) Elagamey, A. G. A.; Abdel-Ghany, A.; Sofan, M. A.; Kandeel, Z. E.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1987, 52, 1561-1565. (h) Sadek, K. U.; Hafez, E. A. A.; Mourad Abo-Elfetouh, E.; Elnagdi, M. H. Z. Naturforsch. B 1984, 39, 824-828. (i) Negm, A. M.; Abd El-Aal, F. A. E.-M.; Hafez, E. A.; Elnagdi, M. H.; Mostafa, J. M. N. Phosphorus, Sulfur, Silicon 1995, 106, 1-7.
17. For Michael adducts or retro-Michael addition products from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Goncharenko, M. P.; Sharanin, Yu. A.; Turov, A. V. Zh. Org. Khim. 1993, 29, 1610-1618; Russ. J. Org. Chem. 1993, 29, 1341-1347. (b) Michaud, D.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1997, 38, 7563-7564. (c) El-Shafei, A. K.; El-Sayed, A. M.; Sultan, A.; Abdel-Ghany, H. Gazz. Chim. Ital. 1990, 120, 197-201. (d) Ma̧kosza, M.; Kwast, A. Tetrahedron 1991, 47, 5001-5018. (e) Martín, N.; Quinteiro, M.; Seoane, C.; Soto, J. L. Liebigs Ann. Chem. 1990, 101-104. (f) Bogdanowicz-Szwed, K.; Czarny, A. J. Prakt. Chem. 1993, 335, 279-282. (g) Elagamey, A. G. A.; Abdel-Ghany, A.; Sofan, M. A.; Kandeel, Z. E.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1987, 52, 1561-1565. (h) Sadek, K. U.; Hafez, E. A. A.; Mourad Abo-Elfetouh, E.; Elnagdi, M. H. Z. Naturforsch. B 1984, 39, 824-828. (i) Negm, A. M.; Abd El-Aal, F. A. E.-M.; Hafez, E. A.; Elnagdi, M. H.; Mostafa, J. M. N. Phosphorus, Sulfur, Silicon 1995, 106, 1-7.
18. For Michael adducts or retro-Michael addition products from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Goncharenko, M. P.; Sharanin, Yu. A.; Turov, A. V. Zh. Org. Khim. 1993, 29, 1610-1618; Russ. J. Org. Chem. 1993, 29, 1341-1347. (b) Michaud, D.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1997, 38, 7563-7564. (c) El-Shafei, A. K.; El-Sayed, A. M.; Sultan, A.; Abdel-Ghany, H. Gazz. Chim. Ital. 1990, 120, 197-201. (d) Ma̧kosza, M.; Kwast, A. Tetrahedron 1991, 47, 5001-5018. (e) Martín, N.; Quinteiro, M.; Seoane, C.; Soto, J. L. Liebigs Ann. Chem. 1990, 101-104. (f) Bogdanowicz-Szwed, K.; Czarny, A. J. Prakt. Chem. 1993, 335, 279-282. (g) Elagamey, A. G. A.; Abdel-Ghany, A.; Sofan, M. A.; Kandeel, Z. E.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1987, 52, 1561-1565. (h) Sadek, K. U.; Hafez, E. A. A.; Mourad Abo-Elfetouh, E.; Elnagdi, M. H. Z. Naturforsch. B 1984, 39, 824-828. (i) Negm, A. M.; Abd El-Aal, F. A. E.-M.; Hafez, E. A.; Elnagdi, M. H.; Mostafa, J. M. N. Phosphorus, Sulfur, Silicon 1995, 106, 1-7.
19. For Michael adducts or retro-Michael addition products from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Goncharenko, M. P.; Sharanin, Yu. A.; Turov, A. V. Zh. Org. Khim. 1993, 29, 1610-1618; Russ. J. Org. Chem. 1993, 29, 1341-1347. (b) Michaud, D.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1997, 38, 7563-7564. (c) El-Shafei, A. K.; El-Sayed, A. M.; Sultan, A.; Abdel-Ghany, H. Gazz. Chim. Ital. 1990, 120, 197-201. (d) Ma̧kosza, M.; Kwast, A. Tetrahedron 1991, 47, 5001-5018. (e) Martín, N.; Quinteiro, M.; Seoane, C.; Soto, J. L. Liebigs Ann. Chem. 1990, 101-104. (f) Bogdanowicz-Szwed, K.; Czarny, A. J. Prakt. Chem. 1993, 335, 279-282. (g) Elagamey, A. G. A.; Abdel-Ghany, A.; Sofan, M. A.; Kandeel, Z. E.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1987, 52, 1561-1565. (h) Sadek, K. U.; Hafez, E. A. A.; Mourad Abo-Elfetouh, E.; Elnagdi, M. H. Z. Naturforsch. B 1984, 39, 824-828. (i) Negm, A. M.; Abd El-Aal, F. A. E.-M.; Hafez, E. A.; Elnagdi, M. H.; Mostafa, J. M. N. Phosphorus, Sulfur, Silicon 1995, 106, 1-7.
20. For Michael adducts or retro-Michael addition products from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Goncharenko, M. P.; Sharanin, Yu. A.; Turov, A. V. Zh. Org. Khim. 1993, 29, 1610-1618; Russ. J. Org. Chem. 1993, 29, 1341-1347. (b) Michaud, D.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1997, 38, 7563-7564. (c) El-Shafei, A. K.; El-Sayed, A. M.; Sultan, A.; Abdel-Ghany, H. Gazz. Chim. Ital. 1990, 120, 197-201. (d) Ma̧kosza, M.; Kwast, A. Tetrahedron 1991, 47, 5001-5018. (e) Martín, N.; Quinteiro, M.; Seoane, C.; Soto, J. L. Liebigs Ann. Chem. 1990, 101-104. (f) Bogdanowicz-Szwed, K.; Czarny, A. J. Prakt. Chem. 1993, 335, 279-282. (g) Elagamey, A. G. A.; Abdel-Ghany, A.; Sofan, M. A.; Kandeel, Z. E.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1987, 52, 1561-1565. (h) Sadek, K. U.; Hafez, E. A. A.; Mourad Abo-Elfetouh, E.; Elnagdi, M. H. Z. Naturforsch. B 1984, 39, 824-828. (i) Negm, A. M.; Abd El-Aal, F. A. E.-M.; Hafez, E. A.; Elnagdi, M. H.; Mostafa, J. M. N. Phosphorus, Sulfur, Silicon 1995, 106, 1-7.
21. For Michael adducts or retro-Michael addition products from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Goncharenko, M. P.; Sharanin, Yu. A.; Turov, A. V. Zh. Org. Khim. 1993, 29, 1610-1618; Russ. J. Org. Chem. 1993, 29, 1341-1347. (b) Michaud, D.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1997, 38, 7563-7564. (c) El-Shafei, A. K.; El-Sayed, A. M.; Sultan, A.; Abdel-Ghany, H. Gazz. Chim. Ital. 1990, 120, 197-201. (d) Ma̧kosza, M.; Kwast, A. Tetrahedron 1991, 47, 5001-5018. (e) Martín, N.; Quinteiro, M.; Seoane, C.; Soto, J. L. Liebigs Ann. Chem. 1990, 101-104. (f) Bogdanowicz-Szwed, K.; Czarny, A. J. Prakt. Chem. 1993, 335, 279-282. (g) Elagamey, A. G. A.; Abdel-Ghany, A.; Sofan, M. A.; Kandeel, Z. E.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1987, 52, 1561-1565. (h) Sadek, K. U.; Hafez, E. A. A.; Mourad Abo-Elfetouh, E.; Elnagdi, M. H. Z. Naturforsch. B 1984, 39, 824-828. (i) Negm, A. M.; Abd El-Aal, F. A. E.-M.; Hafez, E. A.; Elnagdi, M. H.; Mostafa, J. M. N. Phosphorus, Sulfur, Silicon 1995, 106, 1-7.
22. For Michael adducts or retro-Michael addition products from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Goncharenko, M. P.; Sharanin, Yu. A.; Turov, A. V. Zh. Org. Khim. 1993, 29, 1610-1618; Russ. J. Org. Chem. 1993, 29, 1341-1347. (b) Michaud, D.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1997, 38, 7563-7564. (c) El-Shafei, A. K.; El-Sayed, A. M.; Sultan, A.; Abdel-Ghany, H. Gazz. Chim. Ital. 1990, 120, 197-201. (d) Ma̧kosza, M.; Kwast, A. Tetrahedron 1991, 47, 5001-5018. (e) Martín, N.; Quinteiro, M.; Seoane, C.; Soto, J. L. Liebigs Ann. Chem. 1990, 101-104. (f) Bogdanowicz-Szwed, K.; Czarny, A. J. Prakt. Chem. 1993, 335, 279-282. (g) Elagamey, A. G. A.; Abdel-Ghany, A.; Sofan, M. A.; Kandeel, Z. E.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1987, 52, 1561-1565. (h) Sadek, K. U.; Hafez, E. A. A.; Mourad Abo-Elfetouh, E.; Elnagdi, M. H. Z. Naturforsch. B 1984, 39, 824-828. (i) Negm, A. M.; Abd El-Aal, F. A. E.-M.; Hafez, E. A.; Elnagdi, M. H.; Mostafa, J. M. N. Phosphorus, Sulfur, Silicon 1995, 106, 1-7.
23. For Michael adducts or retro-Michael addition products from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Goncharenko, M. P.; Sharanin, Yu. A.; Turov, A. V. Zh. Org. Khim. 1993, 29, 1610-1618; Russ. J. Org. Chem. 1993, 29, 1341-1347. (b) Michaud, D.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1997, 38, 7563-7564. (c) El-Shafei, A. K.; El-Sayed, A. M.; Sultan, A.; Abdel-Ghany, H. Gazz. Chim. Ital. 1990, 120, 197-201. (d) Ma̧kosza, M.; Kwast, A. Tetrahedron 1991, 47, 5001-5018. (e) Martín, N.; Quinteiro, M.; Seoane, C.; Soto, J. L. Liebigs Ann. Chem. 1990, 101-104. (f) Bogdanowicz-Szwed, K.; Czarny, A. J. Prakt. Chem. 1993, 335, 279-282. (g) Elagamey, A. G. A.; Abdel-Ghany, A.; Sofan, M. A.; Kandeel, Z. E.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1987, 52, 1561-1565. (h) Sadek, K. U.; Hafez, E. A. A.; Mourad Abo-Elfetouh, E.; Elnagdi, M. H. Z. Naturforsch. B 1984, 39, 824-828. (i) Negm, A. M.; Abd El-Aal, F. A. E.-M.; Hafez, E. A.; Elnagdi, M. H.; Mostafa, J. M. N. Phosphorus, Sulfur, Silicon 1995, 106, 1-7.
24. For Michael adducts or retro-Michael addition products from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Goncharenko, M. P.; Sharanin, Yu. A.; Turov, A. V. Zh. Org. Khim. 1993, 29, 1610-1618; Russ. J. Org. Chem. 1993, 29, 1341-1347. (b) Michaud, D.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1997, 38, 7563-7564. (c) El-Shafei, A. K.; El-Sayed, A. M.; Sultan, A.; Abdel-Ghany, H. Gazz. Chim. Ital. 1990, 120, 197-201. (d) Ma̧kosza, M.; Kwast, A. Tetrahedron 1991, 47, 5001-5018. (e) Martín, N.; Quinteiro, M.; Seoane, C.; Soto, J. L. Liebigs Ann. Chem. 1990, 101-104. (f) Bogdanowicz-Szwed, K.; Czarny, A. J. Prakt. Chem. 1993, 335, 279-282. (g) Elagamey, A. G. A.; Abdel-Ghany, A.; Sofan, M. A.; Kandeel, Z. E.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1987, 52, 1561-1565. (h) Sadek, K. U.; Hafez, E. A. A.; Mourad Abo-Elfetouh, E.; Elnagdi, M. H. Z. Naturforsch. B 1984, 39, 824-828. (i) Negm, A. M.; Abd El-Aal, F. A. E.-M.; Hafez, E. A.; Elnagdi, M. H.; Mostafa, J. M. N. Phosphorus, Sulfur, Silicon 1995, 106, 1-7.
25. For 4H-pyrans from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Martin, N.; Seoane, C.; Soto, J. L. Tetrahedron 1988, 44, 5861-5868. (b) Zayed, S. E.; Elmaged, E. I. A.; Metwally, S. A.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1991, 56, 2175-2182. (c) Assy, M. G.; Hassanien, M. M.; Zaki, S. A. Pol. J. Chem. 1995, 69, 371-375. (d) Quintela, J. M.; Peinador, C.; Moreira, M. J. Tetrahedron 1995, 51, 5901-5912. (e) Elnagdi, M. H.; Aal, F. A. M. A.; Yassin, M. Y. J. Prakt. Chem. 1989, 351, 971-976. (f) Suárez, M.; Molero, D.; Salfran, E.; Martín, N.; Verdecia, Y.; Martinez, R.; Ochoa, E.; Alba, L.; Quinteiro, M.; Seoane, C. Magn. Reson. Chem. 2001, 39, 105-108. (g) Marco, J. L.; Chinchon, P. M. Heterocycles 1999, 51, 1137-1140. (h) Martín, N.; Pascual, C.; Seoane, C.; Soto, J. L. Heterocycles 1987, 26, 2811-2816.
26. For 4H-pyrans from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Martin, N.; Seoane, C.; Soto, J. L. Tetrahedron 1988, 44, 5861-5868. (b) Zayed, S. E.; Elmaged, E. I. A.; Metwally, S. A.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1991, 56, 2175-2182. (c) Assy, M. G.; Hassanien, M. M.; Zaki, S. A. Pol. J. Chem. 1995, 69, 371-375. (d) Quintela, J. M.; Peinador, C.; Moreira, M. J. Tetrahedron 1995, 51, 5901-5912. (e) Elnagdi, M. H.; Aal, F. A. M. A.; Yassin, M. Y. J. Prakt. Chem. 1989, 351, 971-976. (f) Suárez, M.; Molero, D.; Salfran, E.; Martín, N.; Verdecia, Y.; Martinez, R.; Ochoa, E.; Alba, L.; Quinteiro, M.; Seoane, C. Magn. Reson. Chem. 2001, 39, 105-108. (g) Marco, J. L.; Chinchon, P. M. Heterocycles 1999, 51, 1137-1140. (h) Martín, N.; Pascual, C.; Seoane, C.; Soto, J. L. Heterocycles 1987, 26, 2811-2816.
27. For 4H-pyrans from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Martin, N.; Seoane, C.; Soto, J. L. Tetrahedron 1988, 44, 5861-5868. (b) Zayed, S. E.; Elmaged, E. I. A.; Metwally, S. A.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1991, 56, 2175-2182. (c) Assy, M. G.; Hassanien, M. M.; Zaki, S. A. Pol. J. Chem. 1995, 69, 371-375. (d) Quintela, J. M.; Peinador, C.; Moreira, M. J. Tetrahedron 1995, 51, 5901-5912. (e) Elnagdi, M. H.; Aal, F. A. M. A.; Yassin, M. Y. J. Prakt. Chem. 1989, 351, 971-976. (f) Suárez, M.; Molero, D.; Salfran, E.; Martín, N.; Verdecia, Y.; Martinez, R.; Ochoa, E.; Alba, L.; Quinteiro, M.; Seoane, C. Magn. Reson. Chem. 2001, 39, 105-108. (g) Marco, J. L.; Chinchon, P. M. Heterocycles 1999, 51, 1137-1140. (h) Martín, N.; Pascual, C.; Seoane, C.; Soto, J. L. Heterocycles 1987, 26, 2811-2816.
28. For 4H-pyrans from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Martin, N.; Seoane, C.; Soto, J. L. Tetrahedron 1988, 44, 5861-5868. (b) Zayed, S. E.; Elmaged, E. I. A.; Metwally, S. A.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1991, 56, 2175-2182. (c) Assy, M. G.; Hassanien, M. M.; Zaki, S. A. Pol. J. Chem. 1995, 69, 371-375. (d) Quintela, J. M.; Peinador, C.; Moreira, M. J. Tetrahedron 1995, 51, 5901-5912. (e) Elnagdi, M. H.; Aal, F. A. M. A.; Yassin, M. Y. J. Prakt. Chem. 1989, 351, 971-976. (f) Suárez, M.; Molero, D.; Salfran, E.; Martín, N.; Verdecia, Y.; Martinez, R.; Ochoa, E.; Alba, L.; Quinteiro, M.; Seoane, C. Magn. Reson. Chem. 2001, 39, 105-108. (g) Marco, J. L.; Chinchon, P. M. Heterocycles 1999, 51, 1137-1140. (h) Martín, N.; Pascual, C.; Seoane, C.; Soto, J. L. Heterocycles 1987, 26, 2811-2816.
29. For 4H-pyrans from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Martin, N.; Seoane, C.; Soto, J. L. Tetrahedron 1988, 44, 5861-5868. (b) Zayed, S. E.; Elmaged, E. I. A.; Metwally, S. A.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1991, 56, 2175-2182. (c) Assy, M. G.; Hassanien, M. M.; Zaki, S. A. Pol. J. Chem. 1995, 69, 371-375. (d) Quintela, J. M.; Peinador, C.; Moreira, M. J. Tetrahedron 1995, 51, 5901-5912. (e) Elnagdi, M. H.; Aal, F. A. M. A.; Yassin, M. Y. J. Prakt. Chem. 1989, 351, 971-976. (f) Suárez, M.; Molero, D.; Salfran, E.; Martín, N.; Verdecia, Y.; Martinez, R.; Ochoa, E.; Alba, L.; Quinteiro, M.; Seoane, C. Magn. Reson. Chem. 2001, 39, 105-108. (g) Marco, J. L.; Chinchon, P. M. Heterocycles 1999, 51, 1137-1140. (h) Martín, N.; Pascual, C.; Seoane, C.; Soto, J. L. Heterocycles 1987, 26, 2811-2816.
30. For 4H-pyrans from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Martin, N.; Seoane, C.; Soto, J. L. Tetrahedron 1988, 44, 5861-5868. (b) Zayed, S. E.; Elmaged, E. I. A.; Metwally, S. A.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1991, 56, 2175-2182. (c) Assy, M. G.; Hassanien, M. M.; Zaki, S. A. Pol. J. Chem. 1995, 69, 371-375. (d) Quintela, J. M.; Peinador, C.; Moreira, M. J. Tetrahedron 1995, 51, 5901-5912. (e) Elnagdi, M. H.; Aal, F. A. M. A.; Yassin, M. Y. J. Prakt. Chem. 1989, 351, 971-976. (f) Suárez, M.; Molero, D.; Salfran, E.; Martín, N.; Verdecia, Y.; Martinez, R.; Ochoa, E.; Alba, L.; Quinteiro, M.; Seoane, C. Magn. Reson. Chem. 2001, 39, 105-108. (g) Marco, J. L.; Chinchon, P. M. Heterocycles 1999, 51, 1137-1140. (h) Martín, N.; Pascual, C.; Seoane, C.; Soto, J. L. Heterocycles 1987, 26, 2811-2816.
31. For 4H-pyrans from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Martin, N.; Seoane, C.; Soto, J. L. Tetrahedron 1988, 44, 5861-5868. (b) Zayed, S. E.; Elmaged, E. I. A.; Metwally, S. A.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1991, 56, 2175-2182. (c) Assy, M. G.; Hassanien, M. M.; Zaki, S. A. Pol. J. Chem. 1995, 69, 371-375. (d) Quintela, J. M.; Peinador, C.; Moreira, M. J. Tetrahedron 1995, 51, 5901-5912. (e) Elnagdi, M. H.; Aal, F. A. M. A.; Yassin, M. Y. J. Prakt. Chem. 1989, 351, 971-976. (f) Suárez, M.; Molero, D.; Salfran, E.; Martín, N.; Verdecia, Y.; Martinez, R.; Ochoa, E.; Alba, L.; Quinteiro, M.; Seoane, C. Magn. Reson. Chem. 2001, 39, 105-108. (g) Marco, J. L.; Chinchon, P. M. Heterocycles 1999, 51, 1137-1140. (h) Martín, N.; Pascual, C.; Seoane, C.; Soto, J. L. Heterocycles 1987, 26, 2811-2816.
32. For 4H-pyrans from reactions of stabilized carbanions with benzylidenemalononitriles, see: (a) Martin, N.; Seoane, C.; Soto, J. L. Tetrahedron 1988, 44, 5861-5868. (b) Zayed, S. E.; Elmaged, E. I. A.; Metwally, S. A.; Elnagdi, M. H. Collect. Czech. Chem. Commun. 1991, 56, 2175-2182. (c) Assy, M. G.; Hassanien, M. M.; Zaki, S. A. Pol. J. Chem. 1995, 69, 371-375. (d) Quintela, J. M.; Peinador, C.; Moreira, M. J. Tetrahedron 1995, 51, 5901-5912. (e) Elnagdi, M. H.; Aal, F. A. M. A.; Yassin, M. Y. J. Prakt. Chem. 1989, 351, 971-976. (f) Suárez, M.; Molero, D.; Salfran, E.; Martín, N.; Verdecia, Y.; Martinez, R.; Ochoa, E.; Alba, L.; Quinteiro, M.; Seoane, C. Magn. Reson. Chem. 2001, 39, 105-108. (g) Marco, J. L.; Chinchon, P. M. Heterocycles 1999, 51, 1137-1140. (h) Martín, N.; Pascual, C.; Seoane, C.; Soto, J. L. Heterocycles 1987, 26, 2811-2816.
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