Rapid and efficient ring opening of epoxides catalyzed by a new electron deficient tin(IV) porphyrin

Tetrahedron

Volumn 60, Issue 29, 2004, Pages 6105-6111

  Moghadam, Majid ^a   Tangestaninejad, Shahram ^b   Mirkhani, Valiollah ^b   Shaibani, Reza ^a  

^a YASOUJ UNIVERSITY   (Iran)

^b UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

Electron deficient metallporphyrin; Epoxide; Ring opening

Indexed keywords

EPOXIDE; PORPHYRIN DERIVATIVE; TIN;

ALCOHOLYSIS; ANALYTIC METHOD; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; ELECTRON; HYDROLYSIS; PRIORITY JOURNAL; RING OPENING;

EID: 3042569035     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.069     Document Type: Article

References (76)

1. Bonini C., Righi G. Synthesis. 1994;225
2. Iranpoor N., Mohammadpour-Baltork I. Synth. Commun. 20:1990;2789
3. Shimizu M., Yoshida A., Fujisawa T. Synlett. 1992;204
4. Munavalli S., Rohrbaugh D.K., Berg F.J., Longo F.R., Durst H.D. Phosphorus, Sulfur Silicon. 177:2002;215. and references cited therein
5. Sharghi H., Nasseri Ali M., Niknam K. J. Org. Chem. 66:2001;7287
6. Hodgson D.M., Gibbs A.R., Lee G.P. Tetrahedron. 52:1996;14361
7. Paterson I., Berrisford D.J. Angew. Chem., Int. Ed. Engl. 31:1992;1197
8. Taylor S.K. Tetrahedron. 56:2000;1149
9. Parker R.E., Isaacs N.S. Chem. Rev. 59:1959;737
10. Smith J.G. Synthesis. 1984;629
11. Rao A.S., Paknikar S.K., Kirtane J.G. Tetrahedron. 39:1983;2323
12. Olah G.A., Fung A.P., Mieder D. Synthesis. 1981;280
13. Posner G.H., Rogers D.Z., Kinzig C.H., Gurria G.M. Tetrahedron Lett. 16:1975;3597
14. Otera J., Yoshida Y., Hirakawa K. Tetrahedron Lett. 26:1985;3219
15. Posner G.H., Rogers D.Z. J. Am. Chem. Soc. 99:1977;8208
16. Posner G.H., Rogers D.Z. J. Am. Chem. Soc. 99:1977;8214
17. Chini M., Crotti P., Favero L., Pineschi M. Tetrahedron Lett. 35:1994;433
18. Iranpoor N., Mohammadpour-Baltork I. Tetrahedron Lett. 31:1990;735
19. Iranpoor N., Mohammadpour-Baltork I., Shiriny Zardaloo F. Tetrahedron. 47:1991;9861
20. Cheudary B.M., Sudha Y. Synth. Commun. 26:1996;2989
21. Iranpoor N., Salehi P. Synthesis. 1994;1152
22. Masaki Y., Miura T., Ochiai M. Synlett. 1993;847
23. Masaki Y., Miura T., Ochiai M. Bull. Chem. Soc. Jpn. 69:1996;195
24. Iranpoor N., Tarrian T., Movahedi Z. Synthesis. 1996;1473
25. Jacobsen E.N., Kakiuchi F., Konsler R.G., Larrow J.F., Tokunaga M. Tetrahedron Lett. 38:1997;773
26. Taniguch Y., Tanaka S., Kitamura T., Fujiwara Y. Tetrahedron Lett. 39:1998;4559
27. Iranpoor N., Shekarriz M., Shiriny F. Synth. Commun. 28:1998;347
28. Mohammadpour-Baltork I., Tangestaninejad S., Aliyan H., Mirkhani V. Synth. Commun. 30:2000;2365
29. Mirkani V., Tangestaninejad S., Yadollahi B., Alipanah L. Tetrahedron. 59:2003;8213
30. Suda K., Sashima M., Izutsu M., Hino F. J. Chem. Soc. Chem. Commun. 1994;949
31. Takanami T., Hirabe R., Ueno M., Hino F., Suda K. Chem. Lett. 1996;1031
32. Firouzabadi H., Sardarian A.R., Khayat Z., Karimi B., Tangestaninejad S. Synth. Commun. 27:1997;2709
33. Firouzabadi H., Khayat Z., Sardarian A.R., Tangestaninejad S. Iran. J. Chem. Chem. Eng. 15:1996;54
34. Tangestaninejad S., Mirkhani V. Synth. Commun. 29:1999;2079
35. Tangestaninejad S., Habibi M.H., Mirkhani V., Moghadam M. J. Chem. Res(S). 2001;365
36. Tangestaninejad S., Habibi M.H., Mirkhani V., Moghadam M. Synth. Commun. 32:2002;1337
37. Tangestaninejad S., Mirkhani V. J. Chem. Res(S). 1999;370
38. Sunder M. Chem. Rev. 66:1966;297
39. Vedegs E., Kraffi G.A. Tetrahedron. 38:1982;2857
40. Jankowski K., Harry R. Synthesis. 1972;627
41. Bouda H., Borredon M.E., Delmas M., Gaset A. Synth. Commun. 19:1989;491
42. Ketcham R., Shah V.P. J. Org. Chem. 28:1963;229
43. Bordwell F.G., Anderson M.H. J. Am. Chem. Soc. 75:1953;4959
44. Chan T.H., Finkenbine J.R. J. Am. Chem. Soc. 94:1972;2880
45. Mohammadpour-Baltork I., Khosropour A.R. Indian J. Chem. 38:1999;605
46. Iranpoor N., Zaynizadeh B. Synth. Commun. 28:1998;3913
47. Tamami B., Kiasat A.R. Synth. Commun. 26:1996;3953
48. Iranpoor N., Kazemi F. Synthesis. 1996;821
49. Iranpoor N., Kazemi F. Tetrahedron. 53:1997;11377
50. Aldrich Catalogue Handbook of Fine Chemicals, 1990-91.
51. CRC Handbook of Chemistry and Physics, 54th ed., CRC Press, 1973.
52. Green T.H., Wuts P.G.M. Protective Groups in Organic Synthesis. 2nd ed. 1991;Wiley, New York. pp 188-195
53. Meskens F.A.J. Synthesis. 1981;501
54. Hanzlik R.P., Leinwetter M. J. Org. Chem. 43:1978;438
55. Zatprski L.W., Wierzchowski P.T. Catal. Lett. 10:1991;211
56. (b) Steinbrink, H.; Chemische Werke Huls, A. G. German Patent (DOS), 1086241, 1959; Chem. Abstr. 1962, 56, 5969.
57. Gevorkyan A.A., Kazarian P.I., Anakyan O.V., Vardanian R.A. Kim. Geterotsikl. Soedin. 1:1991;33. Chem. Abstr., 1991, 115, 8633x
58. Rickborn B., Gerkin R.M. J. Am. Chem. Soc. 93:1971;1693
59. Huderlik P.F., Misra R.N., Withers G.P., Huderlik H.M., Rona R.J., Arcoleo J.P. Tetrahedron Lett. 1976;1453
60. Kagan J., Firth B.E., Shih N.Y., Boyajian C. J. Org. Chem. 42:1977;343
61. Harvey D.J. Res. Commun. Chem. Pathol. Pharmacol. 4:1972;247
62. Torok D.S., Figueroa J.J., Scott W.J. J. Org. Chem. 58:1993;7274
63. Iranpoor N., Kazemi F. Synth. Commun. 28:1998;3189
64. Iranpoor N., Zeynizadeh B. J. Chem. Res.(S). 1998;466
65. Habibi M.H., Tangestaninejad S., Mirkhani V., Yadollahi B. Catal. Lett. 75:2001;205
66. Schuetz R.D., Jacobs R.L. J. Org. Chem. 26:1961;3467
67. Moore C.G., Porter M. J. Chem. Soc. 1958;2062
68. Takido T., Kobayashi Y., Itabashi K. Synthesis. 1986;779
69. Adler A.D., Long F.R., Finarellii J.D., Goldmacher J., Assour J., Korsakoff L. J. Org. Chem. 32:1967;476
70. Adler A.D., Long F.R., Kampas F., Kim J. J. Inorg. Nucl. Chem. 32:1970;2443
71. Movsumzade M.M., Krimova N.G., Shabanov A.L. Azerb. Kim. Zh. 1968;116. C.A. 1969, 71, 124297n
72. Ponomarev F.G. Doklady Akad. Nauk S.S.S.R. 108:1956;648. C. A. 1957, 51, 3565
73. Engler G., Ulsperger E. J. Prak. Chem. 316:1974;325
74. Leggetter E., Brown R.K. Can. J. Chem. 43:1965;1030. C.A. 1965, 63, 593g
75. Buchneau D. Chem. Phys. Lipids. 1:1967;247. C.A. 1968, 68, 2539k
76. Fourneau J.P., Chantalou S. Bull. Soc. Chim. 12:1945;845. C.A. 1946, 40, 6465