Reactions of epoxides and episulfides with electrophilic halogens

Tetrahedron

Volumn 58, Issue 35, 2002, Pages 7037-7042

  Iranpoor, Nasser ^a   Firouzabadi, Habib ^a   Chitsazi, Maryam ^a   Ali Jafari, Abbas ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Alcoholysis dimerization; Electrophilic halogens; Episulfides; Epoxide

Indexed keywords

2,4,4,6 TETRABROMO 2,5 CYCLOHEXADIEN 1 ONE; ALCOHOL; ALKENE DERIVATIVE; BROMINE DERIVATIVE; CHEMICAL COMPOUND; EPOXIDE; FORMIC ACID 1 BROMOMETHYL 2 CHLOROETHYL ESTER; FORMIC ACID 1 BROMOMETHYL 2 ISOPROPYLETHYL ESTER; FORMIC ACID 1 BROMOMETHYL 2 PHENOXYETHYL ESTER; FORMIC ACID 1 BROMOMETHYL 2 VINYLOXYETHYL ESTER; FORMIC ACID 1 BROMOMETHYLPENTYL ESTER; FORMIC ACID 2 BROMO 2 PHENYLETHYL ESTER; FORMIC ACID 2 BROMOCYCLOHEXYL ESTER; FORMIC ACID DERIVATIVE; HALOGEN; IODINE DERIVATIVE; N BROMOSUCCINIMIDE; PHOSPHORUS DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DIMERIZATION; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0037178957     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00699-3     Document Type: Article

References (55)

1. Rosewsky A. Heterocyclic Compounds with Three and Four Membered Rings, Part I. 1964;Interscience, New York. Chapter I.
2. Izydore R.A., Ghirardelli G.R. J. Org. Chem. 38:1973;1790-1793.
3. Sexton A.R., Britton E.C. J. Am. Chem. Soc. 70:1948;3606-3607.
4. Bridger R.F., Russel R.R. J. Org. Chem. 25:1960;863-866.
5. Gilman H., Fullhart L. J. Am. Chem. Soc. 71:1949;1478-1481.
6. Goodman L., Benitez A., Baker B.R. J. Am. Chem. Soc. 80:1958;1680-1687.
7. Bordwell F.G., Anderson H.M. J. Am. Chem. Soc. 75:1953;495-496.
8. Christensen B.G., Strachan R.G., Trenner N.R., Arison B.H., Hir Schmann R., Chemerds J.M. J. Am. Chem. Soc. 82:1960;3995-4000.
9. Norton J.R., Shenton K.E., Schwartz J. Tetrahedron Lett. 1975;51-54.
10. Brown H.C., Krishnamurthy S. Tetrahedron. 35:1979;567-607.
11. Brown H.C., Yoon N.M. J. Am. Chem. Soc. 88:1966;1464-1472.
12. Smith J.C. Synthesis. 1984;629-656.
13. Sander M. Chem. Rev. 66:1966;297-339.
14. (a) Iranpoor N., Mohammadpour Baltork I. Synth. Commun. 20:1990;2789-2797.
15. (b) Iranpoor N., Mohammadpour Baltork I., Shiriny F. Tetrahedron. 47:1991;9861-9866.
16. © Iranpoor N., Mohammadpour Baltork I. Tetrahedron Lett. 31:1990;735-738.
17. (d) Iranpoor N., Owji J. Tetrahedron. 47:1991;149-154.
18. (e) Safavi A., Iranpoor N., Fotuhi L. Bull. Chem. Soc. Jpn. 68:1995;2591-2594.
19. (f) Iranpoor N., Tarrian T., Movahedi Z. Synthesis. 1996;1473-1476.
20. (g) Iranpoor N., Kazemi F. Tetrahedron. 53:1997;11377-11382.
21. (h) Iranpoor N., Tamami B., Niknam K. Can. J. Chem. 75:1997;1913-1919.
22. (i) Iranpoor N., Shakarriz M., Shiriny F. Synth. Commun. 28:1998;347-366.
23. (j) Iranpoor N., Adibi H. Bull. Chem. Soc. Jpn. 73:2000;675-680.
24. (k) Salomon C.J. Synlett. 2001;65-68.
25. (a) Firouzabadi H., Iranpoor N., Karimi B., Hazarkhani H. Synlett. 2000;263-265.
26. (b) Firouzabadi H., Iranpoor N., Hazarkhani H. Synlett. 2001;1641-1643.
27. © Firouzabadi H., Iranpoor N., Hazarkhani H. J. Org. Chem. 66:2001;7527-7529.
28. (d) Iranpoor N., Firouzabadi H., Shaterian H.R. J. Org. Chem. 67:2002;2826-2830.
29. (e) Iranpoor N., Firouzabadi H., Shaterian H.R. Phosphorous, Sulfur Silicon. 177:2002;1047-1071.
30. (f) Firouzabadi H., Iranpoor N., Hazarkhani H., Karimi B. J. Org. Chem. 67:2002;2572-2576.
31. (a) Horner L., Oediger H., Hofmann H. Liebigs Ann. Chem. 626:1959;26-34.
32. (b) Wiley G.A., Hershkowiz R.L., Rein B.M., Chung B.C. J. Am. Chem. Soc. 86:1964;964-965.
33. © Wiley G.A., Rein B.M., Hershkowitz R.L. Tetrahedron Lett. 1964;2509-2513.
34. (d) Kaplan L. J. Org. Chem. 31:1966;3454.
35. (e) Schaefer J.P., Weinberg D.S. J. Org. Chem. 30:1965;2635-2639.
36. (f) Brett D., Downie I.M., Lee J.B.M., Matough F.S. Chem. Lett. 1969;1017-1018.
37. (g) Arain R.A., Hargreaves M.K. J. Chem. Soc. C. 1970;67-70.
38. (h) Sonnet P.E., Oliver J.E. J. Org. Chem. 41:1976;3279-3284.
39. (i) Hrubiec R.T., Smith M.B. J. Org. Chem. 49:1984;431-435.
40. (a) Hanack M., Auchter G. J. Am. Chem. Soc. 107:1985;5238-5245.
41. (b) Sandr J., Viala J. Synth. Commun. 22:1992;2945-2948.
42. © Machinek R., Luttke W. Synthesis. 1975;255-256.
43. (d) Wiely G.A., Hershkowitz R.L., Rein B.M., Chung B.C. J. Am. Chem. Soc. 86:1964;964-965.
44. (e) Hodge P., Khoshdel E. J. Chem. Soc., Perkin Trans. 1. 1984;195-198.
45. (a) Heer M.E., Johnson R.A. J. Org. Chem. 37:1972;310-312.
46. (b) Boeckman R.K. Jr., Ganem B. Tetrahedron Lett. 11:1974;913-916.
47. © Barluenga J., Campos P.J., Gonzalez-Nunez E., Asensio G. Synthesis. 1985;426-428.
48. Caputo R., Ferreri C., Palumbo G. Synth. Commun. 17:1987;1629-1636.
49. Morimura S., Horiuchi H., Murayama K. Bull. Chem. Soc. Jpn. 50:1977;2189-2190.
50. Fernandez I., Garsia B., Munoz S., Pedro J.R., Salud R. Synlett. 1993;489-490.
51. Ziegenble W., Franke W. Chem. Ber. 93:1960;1681-1683.
52. (a) Thakore A.N., Pope A.N.P., Oehlschlager A.C. Tetrahedron. 27:1971;2617-2625
53. (b) Sonnet P.E., Oliver J.E. J. Org. Chem. 41:1976;3279-3283.
54. (a) Palumbo G., Ferreri C., Caputo R. Tetrahedron Lett. 24:1983;1307-1310
55. (b) Caputo R., Ferreri C., Noviello S., Paluma G. Synthesis. 1986;499-501.