Alkylation of carbonyl compounds in water: Formation of C-C and C-O bonds in the presence of surfactants

Chemistry - A European Journal

Volumn 8, Issue 22, 2002, Pages 5204-5210

  Cerichelli, Giorgio ^a   Cerritelli, Simona ^a   Chiarini, Marco ^a   De Maria, Paolo ^b   Fontana, Antonella ^b  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b UNIVERSITY OF CHIETI   (Italy)

Author keywords

Alkylation; Aqueous solutions; C C coupling; C O bond formation; Carbonyl compounds; Micelles

Indexed keywords

HYDROLYSIS; KETONES; SODIUM COMPOUNDS; SUBSTRATES; SURFACE ACTIVE AGENTS; WATER;

ENOLATE INTERMEDIATES;

ALKYLATION;

CARBONYL DERIVATIVE; KETONE DERIVATIVE; SURFACTANT;

ALKYLATION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; LOW TEMPERATURE; PHASE TRANSITION; REACTION ANALYSIS;

EID: 0037112609     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021115)8:22<5204::AID-CHEM5204>3.0.CO;2-C     Document Type: Article

References (37)

1. J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th Ed., Wiley, New York, 1992.
2. R. Keefe, A. J. Kresge, in The Chemistry of Enols (Ed.; Z. Rappoport), Wiley, New York, 1990, pp. 399-480.
3. J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry, 1st ed., Oxford University Press, New York, 2001, p. 668.
4. J. K. Whitesell, M. A. Whitesell, Synthesis 1983, 517-536.
5. P. De Maria, A. Fontana, G. Cerichelli, J. Chem. Soc. Perkin Trans. 2 1997, 2329-2334.
6. M. Bassetti, G. Cerichelli, B. P. Floris, Gazz. Chim. Ital. 1991, 8, 2723-2726.
7. A. R. E. Carey, S. Eustace, R. A. More O'Ferrall, B. A. Murray, J. Chem. Soc. Perkin Trans. 2 1993, 2285-2296.
8. P. De Maria, A. Fontana, G. Siani, unpublished results.
9. P. Di Profio, R. Germani, G. Savelli, G. Cerichelli, M. Chiarini, G. Mancini, C. A. Bunton, N. D. Gillitt, Langmuir 1998, 14, 2662-2669.
10. M. Chiarini, Ph.D. Thesis, Universita' di L'Aquila (Italy), 2000.
11. M. Da Silva Baptista, I. Cuccovia, H. Chaimovich, M. J. Politi, J. Phys. Chem. 1992, 96, 6442-6449.
12. L. Brinchi, P. DiProfio, R. Germani, G. Savelli, C. A. Bunton, Colloids Surfaces A: Physicochem. Eng. Aspects 1998, 132, 303-314.
13. C. A. Bunton, J. Mol. Liq. 1997, 72, 231-249.
14. J. H. Fendler, E. J. Fendler, Catalysis in Micellar and Macromolecular Systems. Academic Press, New York, 1975.
15. L. S. Romsted, A General Kinetic Theory of Rate Enhancements for Reactions Between Organic Substrates and Hydrophilic Ions in Micellar Systems, In Micellization, Solubilization, and Microemulsions, Vol. 2 (Ed.: K. L. Mittal), Plenum Press, New York, 1977, pp. 509-530.
16. R. Bacaloglu, C. A. Bunton, F. Ortega, J. Phys. Chem. 1989, 93, 1497-1502.
17. A. Angeli, R. Cipiciani, R. Germani, G. Savelli, G. Cerichelli, C. A. Bunton, J. Colloid Interface Sci. 1988, 121, 42-48.
18. A. Blasko, C. A. Bunton, H. J. Foroudian, J. Colloid Interface Sci. 1995, 175, 122-130.
19. L. Brinchi, P. Di Profio, F. Micheli, R. Germani, G. Savelli, C. A. Bunton, Eur. J. Org. Chem. 2001, 1115-1120.
20. Y. Chevalier, P. Le Perchec, J. Phys, Chem. 1990, 94. 1768-1774.
21. a) S. Tascioglu, Tetrahedron 1996, 52, 11113-11152:
22. b) J. Lindman, H. Kronberg. Surfactants and Polymers in Aqueous Solution, Wiley, England, 1998.
23. A. R. E. Carey, S. Al-Quatami, R. A. More O'Ferrall, B. A. Murray, J. Chem. Soc. Chem. Commun. 1988, 1097-1098.
24. H. Hart, Z. Rappoport, S. E. Biali in The Chemistry of Enols (Ed.: Z. Rappoport), Wiley, New York, 1990, pp. 481-589.
25. C. A. Bunton, L. S. Romsted, L. Sepulveda, J. Phys. Chem. 1980, 84, 2611-2618.
26. G. Musumarra, D. Pisano, A. R. Katritzky, A. R. Lapucha, F. J. Luxem, R. Murugan, M. Siskin, G. Brons, Tetrahedron Comput. Methodol. 1989, 2, 17-36.
27. E. Diez-Barra, S. Merino, P. Sanchez-Verdû, J. Torres, Tetrahedon 1997, 53, 11437-11448.
28. D. H. Hey, O. C. Musgrave, J. Chem, Soc. 1949, 53, 3156-3161.
29. a) M. Yasuda, K. Hayashi, Y. Katoh, I. Shibata, A. Baba, J. Am. Chem. Soc. 1998, 120, 715-720;
30. b) R. B. Bates, S. R. Taylor, J. Org. Chem. 1993, 58, 4469-4470.
31. H. O. House, M. Gall, H. D. Olmstead, J. Org. Chem. 1971, 36, 2361-2371.
32. J. Corey, T. H. Topie, W. A. Wozniak, J. Am. Chem. Soc. 1955, 77, 5415-5417.
33. a) M. Lasperas, A. Perez-Rubalcaba, M. L. Quiroga-Feijoo, Tetrahedon 1980, 36, 3403-3408;
34. b) V. Meyer, L. Oelkers, Ber. 1888, 21, 1297-1306;
35. c) Y. Sawaki, Y. Ogata, J. Am. Chem. Soc. 1975, 97, 6983-6989.
36. Y. Hoshino, H. Tanaka, N. Takeno, Bull. Chem. Soc. Jpn. 1998, 71, 2923-2928.
37. P. Maslak, R. D. Guthrie, J. Am. Chem. Soc. 1986, 108, 2637-2640.