ZnCl2 as an Efficient Catalyst in the Thiolysis of 1,2-Epoxides by Thiophenol in Aqueous Medium

Synlett

Volumn , Issue 15, 2003, Pages 2292-2296

  Amantini, David ^a   Fringuelli, Francesco ^a   Pizzo, Ferdinando ^a   Tortoioli, Simone ^a   Vaccaro, Luigi ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

1,2 epoxides; Aqueous medium; Catalysis; Thiolysis

Indexed keywords

BETA HYDROXYPHENYLSULFIDE; BETA HYDROXYSULFONE; BETA HYDROXYSULFOXIDE; COBALT; COPPER; CYCLOHEXANE OXIDE; EPOXIDE; HYDROGEN PEROXIDE; NICKEL; SULFIDE; SULFONE; SULFOXIDE; THIOPHENOL; UNCLASSIFIED DRUG; WATER; ZINC CHLORIDE;

AQUEOUS SOLUTION; ARTICLE; CATALYST; ENVIRONMENTAL HEALTH; LYSIS; OXIDATION; PH; REACTION TIME; SYNTHESIS; THIOLYSIS;

EID: 0346749664     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42107     Document Type: Article

References (49)

1. (a) Tundo, P.; Anastas, P. T. In Green Chemistry: Challenging Perspectives; Oxford University Press: Oxford, 1999.
2. (b) DeSimone, J. M. Science 2002, 297, 799.
3. (a) Li, C. J.; Chang, T. H. In Organic Reactions in Aqueous Media; Wiley: New York, 1997.
4. (b) Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Eur. J. Org. Chem. 2001, 439.
5. (a) Fringuelli, F.; Piermatti, O.; Pizzo, F. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
6. (b) Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 1999, 64, 6094.
7. (c) Fringuelli, F.; Pizzo, F.; Vaccaro, L. Synthesis 2000, 646.
8. (d) Fringuelli, F.; Pizzo, F.; Vaccaro, L. Synlett 2000, 311.
9. (e) Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green Chem. 2001, 3, 229.
10. (f) Fringuelli, F.; Matteucci, M.; Piermatti, O.; Pizzo, F.; Burla, M. C. J. Org. Chem. 2001, 66, 4661.
11. (a) Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 6734.
12. (b) Amantini, D.; Fringuelli, F.; Pizzo, F. J. Org. Chem. 2002, 67, 7238.
13. (a) Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 3554.
14. (b) Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 4463.
15. (c) Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 4719.
16. (d) Fringuelli, F.; Pizzo, F.; Vaccaro, L. Tetrahedron Lett. 2001, 42, 1131.
17. (a) Luly, J. R.; Yi, N.; Soderquist, J.; Stein, H.; Cohen, J.; Perun, T. J.; Plattner, J. J. J. Med. Chem. 1987, 30, 1609.
18. (b) Conchillo, A.; Camps, F.; Messeguer, A. J. Org. Chem. 1990, 55, 1728.
19. (a) Corey, E. J.; Clark, D. A.; Goto, G.; Marfat, A.; Mioskowski, C.; Samuelsson, B.; Hammarstroem, S. J. Am. Chem. Soc. 1980, 102, 1436.
20. (b) Corey, E. J.; Clark, D. A.; Goto, G. Tetrahedron Lett. 1980, 21, 3143.
21. (a) Fan, R.; Hou, X.-L. J. Org. Chem. 2003, 68, 726.
22. (b) Yadav, J. S.; Reddy, B. V. S.; Baisha, G. Chem. Lett. 2002, 906.
23. (c) Chanrasekar, S.; Reddy, C. R.; Babu, B. N.; Chandrashekar, G. Tetrahedron Lett. 2002, 43, 3801.
24. (d) Romdhani Younes, M.; Chaabouni, M. M.; Baklouti, A. Tetrahedron Lett. 2001, 42, 3167.
25. 9a
26. (a) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Adv. Synth. Catal. 2002, 344, 379.
27. (b) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Green Chem. 2003, 5, 436.
28. (c) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. J. Org. Chem. 2003, 68, 8248.
29. (a) Suh, J. Acc. Chem. Res. 1992, 25, 273.
30. (b) Handbook of Metal-Ligand Interactions in Biological Fluids; Berthon, G., Ed.; Marcel Dekker: New York, Basel, Hong Kong, 1995.
31. Fringuelli, F.; Pizzo, F.; Rucci, M.; Vaccaro, L. J. Org. Chem. 2003, 68, 7041.
32. (a) Richens, D. T. In The Chemistry of Aqua Ions; Wiley: New York, 1997.
33. (b) Baes, C. F. Jr.; Mesmer, R. E. The Hydrolysis of Cations; Wiley: New York, 1976.
34. Bordwell, F. G.; Hughes, D. L. J. Org. Chem. 1982, 47, 3224.
35. Boyer, B.; Hambardzoumian, A.; Roque, J.; Beylerian, N. Tetrahedron 1999, 55, 6147.
36. (a) Ko, S. Y.; Sharpless, K. B. J. Org. Chem. 1986, 51, 5413.
37. (b) Behrens, C. H.; Sharpless, K. B. J. Org. Chem. 1985, 50, 5696.
38. (c) Page, P. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1990, 1375.
39. Forristal, I.; Lawson, K. R.; Rayner, C. M. Tetrahedron Lett. 1999, 40, 7015.
40. Behrens, C. H.; Ko, S. Y.; Sharpless, K. B.; Walker, F. J. J. Org. Chem. 1985, 50, 5687.
41. (a) Adams, H.; Bell, R.; Cheung, Y.-Y.; Jones, D. N.; Tomkinson, N. C. O. Tetrahedron: Asymmetry 1999, 10, 4129.
42. (b) Alvarez-Ibarra, C.; Cuervo-Rodríguez, R.; Fernández- Monreal, M. C.; Ruiz, M. P. J. Org. Chem. 1994, 59, 7284.
43. (c) Conte, V.; Di Furia, F.; Licini, G.; Modena, G.; Sbampato, G.; Valle, G. Tetrahedron: Asymmetry 1991, 2, 257.
44. (d) Kingsbury, C. A. J. Org. Chem. 1972, 37, 102.
45. (a) Raghavan, S.; Joseph, S. C. Tetrahedron: Asymmetry 2003, 14, 101.
46. (b) Tone, H.; Nishi, T.; Oikawa, Y.; Hikota, M.; Yonemitsu, O. Chem. Pharm. Bull. 1989, 37, 1167.
47. (c) Farnum, D. G.; Veysoglu, T.; Cardé, A. M.; Duhl-Emswiler, B.; Pancoast, T. A.; Reitz, T. J.; Cardé, R. T. Tetrahedron Lett. 1977, 46, 4009.
48. Linden, A.; Kruger, L.; Backvall, J.-E. J. Org. Chem. 2003, 68, 5890.
49. Fringuelli, F.; Germani, R.; Savelli, G.; Pizzo, F. Tetrahedron Lett. 1989, 30, 1427.