Metal-template electrophilic substitution on phenols: Synthesis and crystal structure of bromomagnesium phenolate and its reactive complex with para-isopropylbenzaldehyde

Chemistry - A European Journal

Volumn 3, Issue 8, 1997, Pages 1269-1272

  Bocelli, Gabriele ^b   Cantoni, Andrea ^b   Sartori, Giovanni ^a   Maggi, Raimondo ^a   Bigi, Franca ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b CNR   (Italy)

Author keywords

Crystal structure; Electrophilic aromatic substitutions; Magnesium; Regioselectivity; Template synthesis

Indexed keywords

EID: 0030750821     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030814     Document Type: Article

References (36)

1. a) G. Casnati, G. Casiraghi, A. Pochini, G. Sartori, R. Ungaro, Pure Appl. Chem. 1983, 55, 1677;
2. b) G. Sartori, R. Maggi, F. Bigi, A. Arienti, C. Porta, G. Predieri, Tetrahedron 1994, 50, 10587;
3. G. Sartori, F. Bigi, R. Maggi, A. Pastorio, C. Porta, G. Bonfanti, J. Chem. Soc. Perkin Trans. 1 1994, 1879.
4. a) G. Casiraghi, G. Casnati, M. Cornia, A. Pochini, G. Puglia, G. Sartori, R. Ungaro, J. Chem. Soc. Perkin Trans. 1 1978, 318;
5. b) G. Sartori, G. Casiraghi, L. Bolzoni, G. Casnati, J. Org. Chem. 1979, 44, 803;
6. G. Casiraghi, G. Casnati, G. Puglia, G. Sartori, M. G. Terenghi, J. Chem. Soc. Perkin Trans. 1 1980, 1862.
7. a) W. Nagata, K. Okada, T. Aoki, Synthesis 1979, 365;
8. b) G. Casiraghi, G. Casnati, G. Sartori, L. Bolzoni, J. Chem. Soc. Perkin Trans. 1 1979, 2027;
9. F. Bigi, G. Casiraghi, G. Casnati, G. Sartori, L. Zetta, J. Chem. Soc. Chem. Commun. 1983, 1210;
10. F. Bigi, G. Casiraghi, G. Casnati, G. Sartori, G. Gasparri Fava, M. Ferrari Belicchi, J. Org. Chem. 1985, 50, 5018;
11. e) F. Bigi, G. Casnati, G. Sartori, C. Dalprato, R. Bortolini, Tetrahedron Asymmetry 1990, 1, 861.
12. a) T. Sugasawa, T. Toyoda, M. Adachi, K. Sasakura, J. Am. Chem. Soc. 1978, 100, 4842;
13. b) S. E. Diamond, A. Szolkievicz, F. Mares, ibid. 1979, 101, 490.
14. a) S. Nunomoto, Y. Yamashida, Kogyo Kagaku Zasshi 1970, 73, 1990;
15. b) D. V. Joffe, M. I. Mostova, Russ. Chem. Rev. 1973, 42, 1.
16. E. Dradi, A. Pochini, R. Ungaro, Gazz. Chim. Ital. 1980, 110, 353.
17. G.-J. M. Gruter, G. P. M. van Klink, O. S. Akkerman, F. Bickelhaupt, Chem. Rev. 1995, 95, 2405.
18. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100289. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK (Fax: Int. code +(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).
19. A. L. Spek, P. Voorbergen, G. Schat, C. Blomberg, F. Bickelhaupt, J. Organomet. Chem. 1974, 77, 147.
20. P. G. Williard, J. M. Salvino, J. Chem. Soc. Chem. Commun. 1986, 153.
21. N. A. Bell, P. T. Moseley, H. M. M. Shearer, Acta Crystallogr. 1984, C40, 602.
22. J. Toney, G. D. Stucky, J. Organomet. Chem. 1971, 28, 5.
23. a) E. C. Ashby, J. Am. Chem. Soc. 1965, 91, 4426;
24. b) E. C. Ashby, R. E. Reed, J. Org. Chem. 1966, 31, 971.
25. L. Pauling, The Nature of the Chemical Bond, 3rd ed., Cornell University Press, Ithaca, N. Y., 1960.
26. a) L. J. Guggenberger, R. E. Rundle, J. Am. Chem. Soc. 1968, 90, 5375;
27. b) G. Stucky, R. E. Rundle, ibid. 1964, 86, 4824.
28. R. H. Shannon, Acta Crystallogr. 1976, A32, 751.
29. a) A. W. Duff, P. B. Hitchcock, M. F. Lappert, R. G. Taylor, J. Organomet. Chem. 1985, 293, 271;
30. b) H. F Klein, H. Konig, S. Koppert, K. Ellrich, J. Riede, Organometallics, 1987, 6, 1341;
31. W. Wu, M. Chen, P. Zhou, Organometallics, 1991, 10, 98.
32. D. Belletti, A. Cantoni, G. Pasquinelli, Gestione on line di diffrattometro a cristallo singolo Siemens AED con sistema IBM PS2/30, Centro di Studio per la Strutturistica Diffrattometrica del C. N. R. di Parma, internal report 1/88, 1988.
33. F. Pavelcik, J. Sivy, C. Rizzoli, XFPS90: Computer program for automatic Fourier, Patterson and Superposition method, personal communication, 1990.
34. C. Rizzoli, V. Sangermano, G. Calestani, G. D. Andreetti, J. Appl. Crystallogr. 1987, 20, 436.
35. G. M. Sheldrick, SHELX76: Program for Crystal Structure Determination, University of Cambridge (UK), 1976.
36. P. Gluzinski, X-Ray set of programs for X-ray structural calculations, Polish Academy of Sciences, Warsaw (Poland), 1989.