Ring opening of epoxides with sodium azide in water. A regioselective pH-controlled reaction

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 6094-6096

  Fringuelli, Francesco ^a   Piermatti, Oriana ^a   Pizzo, Ferdinando ^a   Vaccaro, Luigí ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; SODIUM AZIDE;

AQUEOUS SOLUTION; ARTICLE; CYCLIZATION; EPOXIDATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; STEREOSPECIFICITY; TEMPERATURE;

EID: 0033529831     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990368i     Document Type: Article

References (41)

1. (a) The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: New York, 1971.
2. (b) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297.
3. (c) Coe, D. M.; Myers, P. L.; Parry, D. M.; Roberts, S. M.; Storer, R. J. Chem. Soc., Chem. Commun. 1990, 151.
4. (d) Jacobs, G. A.; Tino, J. A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955.
5. (a) Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Eur. J. Org. Chem. 1998, 5, 1675.
6. (b) Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510.
7. (c) Swift, G.; Swern, D. J. Org. Chem. 1967, 32, 511.
8. (a) Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett. 1990, 31, 5641.
9. (b) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc. Chem. Commun. 1995, 1021.
10. (c) Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557.
11. (d) Sinou, D.; Emziane, M. Tetrahedron Lett. 1986, 27, 4423.
12. (e) Blandy, C.; Choukroun, R.; Gervais, D. Tetrahedron Lett. 1983, 24, 4189.
13. (f) Saito, S.; Yamashita, S.; Nishikawa, T.; Yokoyama, Y.; Inaba, M.; Moriwake, T. Tetrahedron Lett. 1989, 30, 4153.
14. (g) Sarangi, C.; Das, N. B.; Nanda, B.; Nayak, A.; Sharma, R. P. J. Chem. Res., Synop. 1997, 378.
15. (a) Caron, M.; Carlier, P. R.; Sharpless, K. B. J. Org. Chem. 1988, 53, 5185.
16. (b) Youn, Y. S.;. Cho, I. S.; Chung, B. Y. Tetrahedron Lett. 1998, 39, 4337.
17. (c) Saito, S.; Nishikawa, T.; Yokoyama, Y.; Moriwake, T. Tetrahedron Lett. 1990, 31, 221.
18. (d) Onaka, M.; Sugita, K.; Izumi, Y. J. Org. Chem. 1989, 54, 1116.
19. (e) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
20. (a) Crotti, P.; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1996, 37, 1675.
21. (b) Mereyala, H. B.; Frei, B. Helv. Chim. Acta 1986, 69, 415.
22. (a) Guy, A.; Doussot, J.; Garreau, R.; Godefroy-Falguieres, A. Tetrahedron: Asymmetry 1992, 3, 247.
23. (b) DeMarinis, R. M.; Berchtold, G. A. J. Am. Chem. Soc. 1969, 91, 6525.
24. (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: Glasgow, 1998.
25. (b) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
26. Fringuelli, F.; Piermatti, O.; Pizzo, F. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: Glasgow, 1998; pp 223-244 and 250-261.
27. Fringuelli, F.; Piermatti, O.; Pizzo, F. In Targets in Heterocyclic Systems; Attanasi, O. A., Spinelli, D., Eds.; SCI: Rome, 1997; pp 57-73.
28. (a) Fringuelli, F.; Germani, R.; Pizzo, F.; Santinelli, F.; Savelli, G. J. Org. Chem. 1992, 57, 1198.
29. (b) Fringuelli, F.; Pellegrino, R.; Pizzo, F. Synth. Commun. 1993, 23, 3157.
30. (c) Ye, D.; Fringuelli, F.; Piermatti, O.; Pizzo, F. J. Org. Chem. 1997, 62, 3748.
31. 12b carefully studied the kinetics of aminolysis and azidolysis of benzo[a]pyrene diol epoxide in 1:9 dioxane/water at several pH values.
32. (a) Blum, J.; Ben-Shoshan, S. J. Heterocycl. Chem. 1983, 20, 1461.
33. (b) Lin, B.; Islam, N.; Friedman, S.; Yagi, H.; Jerina, D. M.; Whalen, D. L. J. Am. Chem. Soc. 1998, 120, 4327.
34. The reaction could occur in the pseudomicellar phase where the hydroxide counterion makes the pH higher than that of the aqueous phase.
35. 3 significantly increases the pH of the medium.
36. (b) Handbook of Chemistry and Physics, 78th ed.; Lide, D. R., Ed.; CRC Press: New York, 1997-98; pp 8-45.
37. (a) Fringuelli, F.; Germani, R.; Pizzo, F.; Savelli, G. Tetrahedron Lett. 1989, 30, 1427.
38. (b) Fringuelli, F.; Pizzo, F.; Germani, R.; Savelli, G. Org. Prep. Proced. Int. 1989, 30, 757.
39. (a) Fringuelli, F.; Piermatti, O.; Pizzo, F. Gazz. Chim. Ital. 1995, 125, 195.
40. (b) Fringuelli, F.; Gottlieb, H. B.; Hagaman, E. W.; Taticchi, A., Wenkert, E.; Workulich, P. M. Gazz. Chim. Ital. 1975, 105, 1215.
41. (c) Fringuelli, F.; Moreno, L. N.; Taticchi, A.; Wenkert, E. J. Org. Chem. 1977, 42, 3168.