Conversion of epoxides into halohydrins with elemental halogen catalyzed by thiourea

Tetrahedron

Volumn 59, Issue 43, 2003, Pages 8509-8514

  Sharghi, Hashem ^a   Eskandari, Mohammad Mehdi ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Epoxide; Halohydrins; Thiourea

Indexed keywords

BROMINE DERIVATIVE; EPOXIDE; HALOGEN; IODINE DERIVATIVE; THIOUREA;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; GAS CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0141619393     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.033     Document Type: Article

References (46)

1. Bonini C., Righi G. Synthesis. 1994;225-241.
2. (a) Shimizu M., Yoshida A., Fujisawa T. Synlett. 1992;204-206
3. (b) Iranpoor N., Mohammadpour Baltork I. Synth. Commun. 20:1990;2789-2797.
4. For an exhaustive list of methods for the preparation of 1,2-halohydrins from epoxides see: Smith J.G., Fieser M. Fieser and Fieser's Reagent for Organic Synthesis. Collective Index for Vols. 1-12:1990;Wiley, New York.
5. (a) Kricheldorf H.R., Morber G., Regel W. Synthesis. 1981;383-384
6. (b) Andrews G.C., Crawford T.C., Contillo L.G. Tetrahedron Lett. 22:1981;3803-3806
7. (c) Detty M.R., Seidler M.D. Tetrahedron Lett. 23:1982;2543-2546.
8. (a) Palumbo G., Ferreri C., Caputo R. Tetrahedron Lett. 24:1983;1307-1310
9. (b) Caputo R., Ferreri C., Noviello S., Palumbo G. Synthesis. 1986;499-501.
10. (a) Guindon Y., Therien M., Girard Y., Yoakim C. J. Org. Chem. 52:1987;1680-1686
11. (b) Joshi N.N., Srebnik M., Brown H.C. J. Am. Chem. Soc. 110:1988;6246-6248.
12. Bell T.W., Ciaccio J.A. Tetrahedron Lett. 27:1986;827-830.
13. Bovicelli P., Mincione E., Ortaggi G. Tetrahedron Lett. 32:1991;3719-3722.
14. (a) Ciaccio J.A., Heller E., Talbot A. Synlett. 1991;248
15. (b) Shimizu M., Yoshida A., Fugisawa T. Synlett. 1992;204-206
16. (c) Guo Z.X., Haines A.H., Taylor R.J.K. Synlett. 1993;607-608.
17. (a) Bajwa J.S., Anderson R.C. Tetrahedron Lett. 32:1991;3021-3024
18. (b) Kotsuki H., Shimanouchi T. Tetrahedron Lett. 37:1996;1845-1848.
19. Konnaklieva M.I., Dahi M.L., Turos E. Tetrahedron Lett. 33:1992;7093-7096. and references therein.
20. Sharghi H., Niknam K., Pooyan M. Tetrahedron. 57:2001;6057-6064.
21. Dela More P.B.D., Bolton R. Electrophilic Addition to Unsaturated System. 1982;Elsevier, Amsterdam.
22. Eisch J.J., Liu Z.R., Ma X., Zheng G.X. J. Org. Chem. 57:1992;5140-5144.
23. Chini M., Crotti P., Gardelli C., Macchia F. Tetrahedron. 48:1992;3805-3812.
24. (a) Sharghi H., Massah A.R., Abedi M. Talanta. 49:1999;531
25. (b) Semnani A., Shamsipur M. J. Chem. Soc. Dalton Trans. 1996;2215-2218
26. (c) Gangali M.R., Sharghi H., Eshghi H., Shamsipur M. J. Electronal. Chem. 405:1996;177.
27. Serguchev Y.A., Petrenko T.I. Teor. Eksp. Khim. 13:1977;705.
28. Andrews L.J., Keefer R.M. J. Org. Chem. 52:1987;2690-2694.
29. Mizuno M., Tanaka J., Harada I. J. Phys. Chem. 85:1981;1789-1794.
30. Masuda H., Takase K., Nishio M., Hasegavw A., Nishiyama Y., Ishii Y. J. Org. Chem. 59:1994;5550-5555.
31. Golumbic C., Cottle D.L. J. Am. Chem. Soc. 61:1939;996-1000.
32. Guss C.O., Rosenthal R. J. Am. Chem. Soc. 77:1955;2549.
33. Forgo, I.; Buechi, J. Chem. Abstr. 1970, 72, 110733k.
34. Winstein S., Grunwald E., Buckles R.E., Hason C. J. Am. Chem. Soc. 70:1948;816-821.
35. Naqui S.M., Horwitz J.P., Filler R. J. Am. Chem. Soc. 79:1957;6283-6286.
36. Pfeiffer P., Bauer K. Chem. Ber. 80:1947;7. Chem. Abstr. 1947, 41, 3098d.
37. Lide, R. D. CRC Handbook of Chemistry and Physics, 80th ed. 1999-2000.
38. WWW.aist.go.jp/RIODBS/SDBS/sdbs/owa/sdbs-Sea.Ere-Frame-Sea .
39. Koelsch C.F., Mc Elvain S.M. J. Am. Chem. Soc. 51:1929;3390-3394.
40. Lamrrd P.B.D.D.E., Naylor P.G., Williams D.L.H. J. Chem. Soc. 1962;443-449.
41. Woolard F.X., Moore R.E. Tetrahedron. 32:1976;2843-2846.
42. Cornforth, J. W.; Green, D. T. Chem. Abstr. 1970, 72, 121250b.
43. Dawe R.D., Molinski T.F., Turner J.V. Tetrahedron Lett. 25:1984;2061-2064.
44. Iranpoor N., Zeynizadeh B. J. Chem. Res. 1998;466-467. and references therein.
45. Bonini C., Giuliano C., Righi G., Rossi L. Synth. Commun. 22:1992;1863-1870. and references therein.
46. Cowell A., Stille J.K. J. Am. Chem. Soc. 102:1980;4193. and references therein.