An environmentally benign catalytic method for efficient and selective nucleophilic ring opening of oxiranes by zirconium tetrakis(dodecyl Sulfate)

Helvetica Chimica Acta

Volumn 93, Issue 3, 2010, Pages 405-413

  Jafarpour, Maasoumeh ^a   Rezaeifard, Abdolreza ^a   Aliabadi, Marzieh ^a  

^a UNIVERSITY OF BIRJAND   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALCOHOL; CATALYTIC AMOUNTS; CHEMOSELECTIVE; DODECYL SULFATE; ENVIRONMENTALLY BENIGN; HIGH EFFICIENCY; NUCLEOPHILIC RING OPENING; OXIRANES; PRODUCT YIELDS; RING OPENING REACTION; TETRAKIS;

CATALYSTS; REUSABILITY; SULFUR COMPOUNDS;

ZIRCONIUM;

ALCOHOL DERIVATIVE; DODECYL SULFATE; ETHYLENE OXIDE DERIVATIVE; LEWIS ACID; NUCLEOPHILE; SODIUM AZIDE; SODIUM CYANIDE; SURFACTANT; WATER; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ENVIRONMENT; CHEMICAL REACTION; PRIORITY JOURNAL; RING OPENING;

EID: 77949518987     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.200900239     Document Type: Article

References (69)

1. S. Kobayashi, T. Wakabayashi, S. Nagayama, H. Oyamada, Tetrahedron Lett. 1997, 38, 4559.
2. G. Sharma, R. Kumar, A. K. Chakraborti, Tetrahedron Lett. 2008, 49, 4269.
3. S. Kobayashi, T. Wakabayashi, H. Oyamada, Chem. Lett. 1997, 831.
4. K. Manabe, Y. Mori, T.Wakabayashi, S. Nagayama, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 7202.
5. K. Manabe, S. Kobayashi, Chem. - Eur. J. 2002, 8, 4094.
6. Y. Mori, K. Kakumoto, K. Manabe, S. Kobayashi, Tetrahedron Lett. 2000, 41, 3107.
7. K. Manabe, Y. Mori, S. Kobayashi, Tetrahedron 1999, 55, 11203.
8. K. Manabe, S. Kobayashi, Synlett 1999, 547.
9. S. Kobayashi, K. Manabe, Acc. Chem. Res. 2002, 35, 209.
10. K. Manabe, N. Aoyama, S. Kobayashi, Adv. Synth. Catal. 2001, 343, 174.
11. A. Takasu, A. Takemoto, T. Hirabayashi, Biomacromolecules 2006, 7, 6.
12. K. Manabe, S. Kobayashi, Chem. Commun. 2000, 669.
13. S. Kobayashi, Y. Mori, S. Nagayama, K. Manabe, Green Chem. 1999, 175.
14. K. Manabe, Y. Mori, S. Kobayashi, Synlett 1999, 1401.
15. J. E. Huheey, 'Inorganic Chemistry: Principles of Structure and Reactivity', 3rd edn., Harper &Row, Singapore, 1990, Chapt. 7.
16. J. P. Riley, R. Chester, 'Introduction to Marine Chemistry', Academic Press, New York, 1971.
17. R. J. S. R. Lewis, 'Dangerous Properties of Industrial Materials', 8th edn., Van Nostrand Reinhold Co., New York, 1989, Vol. 3.
18. U. Bora, Synlett 2003, 1073, and refs. cit. therein.
19. H. Firouzabadi, M. Jafarpour, J. Iran. Chem. Soc. 2008, 5, 159, and refs. cit. therein.
20. G. Smitha, S. Chandrasekhar, C. S. Reddy, Synthesis 2008, 829, and refs. cit. therein.
21. H. Firouzabadi, N. Iranpoor, M. Jafarpour, A. Ghaderi, J. Mol. Catal., A 2006, 253, 249.
22. H. Firouzabadi, N. Iranpoor, M. Jafarpour, Tetrahedron Lett. 2004, 45, 7451.
23. H. Firouzabadi, N. Iranpoor, M. Jafarpour, Tetrahedron Lett. 2005, 46, 4107.
24. H. Firouzabadi, N. Iranpoor, M. Jafarpour, Tetrahedron Lett. 2006, 47, 93.
25. H. Firouzabadi, N. Iranpoor, M. Jafarpour, J. Sulfur Chem. 2005, 26, 313.
26. H. Firouzabadi, N. Iranpoor, M. Jafarpour, A. Ghaderi, J. Mol. Catal., A 2006, 252, 150.
27. M. Jafarpour, A. Rezaeifard, M. Aliabadi, Lett. Org. Chem. 2009, 6, 94.
28. M. Jafarpour, A. Rezaeifard, T. Golshani, J. Heterocycl. Chem. 2009, 46, 535.
29. S. Bonollo, F. Fringuelli, F. Pizzo, L. Vaccaro, Synlett 2007, 2683, and refs. cit. therein.
30. Y. Permana, S. Shimazu, N. Ichikuni, T. Uematsu, Catal. Commun. 2005, 6, 426, and refs. cit. therein.
31. A. K. Chakraborti, A. Kondaskar, Tetrahedron Lett. 2003, 44, 8315.
32. E. J. Corey, X.-M. Cheng, 'The Logic of Chemical Synthesis', John Wiley & Sons, New York, 1989.
33. T. Kino,H. Hatanaka, M. Hashimoto,M. Nishiyama, T. Goto,M. Okuhara, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1987, 40, 1249.
34. C. Jaramillo, J.-L. Chiara, M. Martin-Lomas, J. Org. Chem. 1994, 59, 3135.
35. C. Moberg, L. Rákos, L. Tottie, Tetrahedron Lett. 1992, 33, 2191.
36. N. Iranpoor, P. Salehi, Synthesis 1994, 1152.
37. N. Iranpoor, T. Tarrian, Z. Movahedi, Synthesis 1996, 1473.
38. N. Iranpoor, H. Adibi, Bull. Chem. Soc. Jpn. 2000, 73, 675.
39. B. M. Choudary, Y. Sudha, Synth. Commun. 1996, 26, 2989.
40. N. Iranpoor, M. Shekarriz, F. Shiriny, Synth. Commun. 1998, 28, 347.
41. N. Iranpoor, I. Mohammadpour Baltork, F. Shiriny, Y. Zardaloo, Tetrahedron 1991, 47, 9861.
42. V. Mirkhani, S. Tangestaninejad, B. Yadollahi, L. Alipanah, Tetrahedron 2003, 59, 8213.
43. B. Tamami, N. Iranpoor, M. A. Karimi Zarchi, Polym. Rep. 1993, 34, 2011.
44. M. L. Kantam, K. Aziz, K. Jeyalakshmi, P. R. Likhar, Catal. Lett. 2003, 89, 95.
45. J. G. Smith, Synthesis 1984, 629.
46. H. Firouzabadi, N. Iranpoor, A. A. Jafari, S. Makarem, J. Mol. Catal., A 2006, 250, 237.
47. J. Barluenga, H. Vázquez-Villa, A. Ballesteros, J. M. Gonzá lez, Org. Lett. 2002, 4, 2817.
48. C. J. Salomon, Synlett 2001, 65.
49. J. S. Yadav, B. V. S. Reddy, K. Harikishan, C. Madan, A. V. Narsaiah, Synthesis 2005, 2897.
50. M.W. C. Robinson, R. Buckle, I.Mabbett,G.M.Grant,A. E.Graham, Tetrahedron Lett. 2007, 48, 4723.
51. P. R. Likhar, M. P. Kumar, A. K. Bandyopadhyay, Synlett 2001, 836.
52. S. C. Bergmeier, Tetrahedron 2000, 56, 2561.
53. D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835.
54. L. S. Goodman, A. Gilman, 'The Pharmacological Basis of Therapeutics', 6th edn., MacMillan, New York, 1980.
55. G. A. Rogers, S. M. Parson, D. C. Anderson, L. M. Nilsson, B. A. Bhar, W. D. Kornreich, R. Kaufman, R. S. Jacobs, B. Kirtman, J. Med. Chem. 1989, 32, 1217.
56. C. Auvin-Guette, S. Rebuffat, Y. Prigent, B. Bodo, J. Am. Chem. Soc. 1992, 114, 2170.
57. J. Schubert, R. Schwesinger, H. Prinzbach, Angew. Chem., Int. Ed. 1984, 23, 167.
58. E. J. Corey, R. K. Bakshi, S. Shibata, C. P. Chen, V. K. Singh, J. Am. Chem. Soc. 1987, 109, 7925.
59. S. Chen, U. Nickel, Chem. Commun. 1996, 133.
60. 'The Chemistry of the Azido Group', Ed. S. Patai, John Wiley & Sons, New York, 1971.
61. E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297.
62. D.M. Coe, P. L.Myers,D.M. Parry, S.M.Roberts,R. Storerb, J. Chem. Soc., Chem. Commun. 1990, 151.
63. B. Das, V. S. Reddy, M. Krishnaiah, Y. Koteswara Rao, J. Mol. Catal., A 2007, 270, 89, and refs. cit. therein.
64. Z. Wang, Y.-T. Cui, Z.-B. Xu, J. Qu, J. Org. Chem. 2008, 73, 2270, and refs. cit. therein.
65. J. S. Yadav, B. V. S. Reddy, B. Jyothirmai, M. S. R. Murty, Tetrahedron Lett. 2005, 46, 6559.
66. G. Sabitha, R. S. Babu, M. S. K. Reddy, J. S. Yadav, Synthesis 2002, 2254.
67. G. Sabitha, R. S. Babu, M. Rajkumar, J. S. Yadav, Org. Lett. 2002, 4, 343.
68. B. Srinivas, V. Pavan Kumar, R. Sridhar, K. Surendra, Y. V. D. Nageswar, K. Rama Rao, J. Mol. Catal., A 2007, 261, 1, and refs. cit. therein.
69. M. A. Zolfigol, P. Salehi, A. Ghaderi, M. Shiri, Z. Tanbakouchian, J. Mol. Catal., A 2006, 259, 253.