On the π-π interaction in the benzylation of ketones

Tetrahedron

Volumn 53, Issue 33, 1997, Pages 11437-11448

  Díez Barra, Enrique ^a   Merino, Sonia ^a   Sánchez Verdú, Prado ^a   Torres, José ^a  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; KETONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; ELECTRON; GEOMETRY; PRIORITY JOURNAL;

EID: 0343487688     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00724-2     Document Type: Article

References (24)

1. For recent reports see: Bisson, A. P., Hunter, C. A., J. Chem. Soc., Chem Commun., 1996, 1723; and Díez-Barra, E., de la Hoz, A., Merino, S., Sánchez-Verdú, P., Tetrahedron Lett., 1997, 38, 2359. More references on this topic are quoted in reference 6.
2. For recent reports see: Bisson, A. P., Hunter, C. A., J. Chem. Soc., Chem Commun., 1996, 1723; and Díez-Barra, E., de la Hoz, A., Merino, S., Sánchez-Verdú, P., Tetrahedron Lett., 1997, 38, 2359. More references on this topic are quoted in reference 6.
3. a) Hunter, C.A., Sanders, J.K.M., J. Am. Chem. Soc., 1990, 112, 5525.
4. b) Singh, J., Thornton, J.M., J. Mol. Biol., 1990, 211, 595.
5. c) Hunter, C.A., Singh, J., Thornton, J.M., J. Mol. Biol., 1991, 218, 837.
6. (a) Tucker, J. A., Houk, K. N., Trost, B. M., J. Am. Chem. Soc., 1990, 112, 5465.
7. (b) Lipkowitz, K. B., Cavanaugh, M. W., Baker, B., O'Donnell, M. J., J. Org. Chem., 1991, 56, 5181.
8. (c) Hunter, C. A., Angew. Chem., Ed. Int. Engl., 1993, 32, 1584.
9. (d) Maddaluno, J. F., Gresh, N., Giessner-Prettre, C., J. Org. Chem., 1994, 59, 793.
10. (a) Smithrud, D. B., Diederich, F., J. Am. Chem. Soc., 1990, 112, 339.
11. (b) Ferguson, S. B., Sanford, E. M., Seward, E. M., Diederich, F., J. Am. Chem. Soc., 1991, 113, 5410.
12. (a) Cozzi, F., Siegel, J. S., et al., J. Am. Chem. Soc., 1992, 114, 5729; ibid., 1993, 115, 5330; Angew. Chem., Int. Ed. Engl., 1995, 34, 1019; Pure & Appl. Chem., 1995, 67, 683
13. (a) Cozzi, F., Siegel, J. S., et al., J. Am. Chem. Soc., 1992, 114, 5729; ibid., 1993, 115, 5330; Angew. Chem., Int. Ed. Engl., 1995, 34, 1019; Pure & Appl. Chem., 1995, 67, 683
14. (a) Cozzi, F., Siegel, J. S., et al., J. Am. Chem. Soc., 1992, 114, 5729; ibid., 1993, 115, 5330; Angew. Chem., Int. Ed. Engl., 1995, 34, 1019; Pure & Appl. Chem., 1995, 67, 683
15. (a) Cozzi, F., Siegel, J. S., et al., J. Am. Chem. Soc., 1992, 114, 5729; ibid., 1993, 115, 5330; Angew. Chem., Int. Ed. Engl., 1995, 34, 1019; Pure & Appl. Chem., 1995, 67, 683
16. Díez-Barra, E., de la Hoz, A., Loupy, A., Martínez-González, A., Martínez-Merino, V., Merino, S., Paugam, R., Sánchez-Verdú, P., Sansoulet, J., Torres, J., Tetrahedron, 1997, 53, 3659.
17. Aliquat 336 is essentially constituted of trioctyl methyl ammonium chloride.
18. Bordwell, F.G., Acc. Chem. Res., 1988, 21, 458.
19. Hunter, C. A., Chem. Soc. Rev., 1994, 101.
20. Kohler, E. P., Chadwell, H. M., Organic Synthesis, Coll. Vol. 1, p 79.
21. Yasui, S., Fujii, M., Ohno, A., Bull. Chem. Soc. Jpn., 1987, 60, 4019.
22. Ranu, B. C., Sarkar, A., Tetrahedron. Lett., 1994, 35, 8649.
23. Anderson, W.K., Veysoglu, T., J. Org. Chem., 1973, 38, 2267.
24. b) Thies, R.W., Chiarello, R.H., J. Org. Chem., 1979, 44, 1342.