Catalytic conversion of epoxides to 1,3-dioxolanes with phosphomolybdic acid (PMA) in solution and under solvent-free conditions

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 183, Issue 9, 2008, Pages 2274-2279

  Zeynizadeh, Behzad ^a   Sadighnia, Leila ^a  

^a URMIA UNIVERSITY   (Iran)

Author keywords

1,3 Dioxolanes; Catalytic; Epoxides; Phosphomolybdic acid; Solvent free

Indexed keywords

EID: 49549101127     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500801960554     Document Type: Article

References (44)

1. T. H. Green and P. G. M. Wuts, Protective Groups in Organic Synthesis (Wiley, New York, 2006) 4th ed.
2. F. A. J. Meskens, Synthesis, 501 (1981).
3. R. P. Hanzlik and M. Leinwetter, J. Org. Chem., 43, 438 (1978).
4. A. A. Gevorkyan, P. I. Kazaryan,O. V. Avakyan, and R. A. Vardanyan, Khim. Geterotsikl. Soedin, 1, 33 (1991);
5. Chem. Abstr., 115, 8633x (1991).
6. D. S. Torok, J. J. Figueroa, and W. J. Scott, J. Org. Chem., 58, 7274 (1993).
7. J. R. Vyvyan, J. A. Meyer, and K. D. Meyer, J. Org. Chem., 68, 9144 (2003).
8. (a) M. T. Bogert and R. O. Roblin, J. Am. Chem. Soc., 55, 3741 (1933);
9. (b) T. Bersin and G. Willfang, Chem. Ber., 70, 2167 (1937);
10. (c) G. Willfang, Chem. Ber., 74, 145 (1941).
11. T. Nagata, T. Takai, T. Yamada, K. Imagawa, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 67, 2614 (1994).
12. N. Iranpoor and B. Zeynizadeh, J. Chem. Res., 466 (1998).
13. I. Mohammadpoor-Baltork, A. Khosropour, and H. Aliyan, Synth. Commun., 31, 3411 (2001).
14. L. W. Zatorski and P. T. Wierzchowski, Catal. Lett., 10, 211 (1991).
15. H. Steinbrink, Chemische Werke Huls AG, Ger. Pat. (DOS), 1086241 (1959);
16. Chem. Abstr., 56, 5969 (1962).
17. I. Bucsi, A. Meleg, A. Molnar, and M. Bartok, J. Mol. Catal. A, 168, 47 (2001).
18. H. Firouzabadi, N. Iranpoor, and H. Shaterian, Bull. Chem. Soc. Jpn., 75, 2195 (2002).
19. S. Tangestaninejad, M. Habibi, V. Mirkhani, and M. Moghadam, J. Chem. Res., 365 (2001).
20. S. B. Lee, T. Takata, and T. Endo, Chem. Lett., 2019 (1990).
21. R. Adams, T. Barnard, and K. Brosius, J. Organomet. Chem., 582, 358 (1999).
22. Z. Zhu and J. H. Espenson, Organometallics, 16, 3658 (1997).
23. N. Iranpoor and F. Kazemi, Synth. Commun., 28, 3189 (1998).
24. A. Procopio, R. Dalpozzo, A. D. Nino, L. Maiuolo,M. Nardi, and B. Russo, Adv. Synth. Catal., 347, 1447 (2005).
25. V. Mirkhani, S. Tangestanijejad, B. Yadollahi, and L. Alipanah, Catal. Lett., 91, 129 (2003).
26. M. H. Habibi, S. Tangestaninejad, V. Mirkhani, and B. Yadollahi, Catal. Lett., 75, 205 (2001).
27. G. Li, B.Wang, J.Wang, Y. Ding, L. Yan, and J. Suo, J. Mol. Catal. A, 236, 72 (2005).
28. M. N. Timofeeva, Appl. Catal. A, 256, 19 (2003).
29. (a) I. V. Kozhevnikov, Chem. Rev., 98, 171 (1998);
30. (b) N. Mizuno and M. Misono, Chem. Rev., 98, 199 (1998);
31. (c) C.W. Hu, M. Hashimota, T. Okuhara, and M. Misono, J. Catal., 143, 437 (1993).
32. (a) J. H. Day and T. A. Solak, J. Am. Chem. Soc., 73, 469 (1951);
33. (b) E. F. Murphy, M. Schneider, T. Mallat, and A. Baiker, Synthesis, 547 (2001);
34. (c) T.-S. Jin, Y. -W. Li, G. Sun, and T.- S. Li, J. Chem. Res., 456 (2002);
35. (d) T.-S. Jin, Y.-W. Li, G. Sun, X. -R. Song, and T. -S. Li, J. Chem. Res., 322 (2003);
36. (e) G. D. K. Kumar and S. Baskaran, Synlett, 1719 (2004);
37. (f) A. Defoin, Synthesis, 706 (2004);
38. (g) J. S. Yadav, S. Raghavendra, M. Satyanarayana, and E. Balanarsaiah, Synlett, 2461 (2005);
39. (h) G. D. K. Kumar and S. Baskaran, J. Org. Chem., 70, 4520 (2005);
40. (i) M. M. M. Abd El-Wahab and A. A. Said, J. Mol. Catal. A, 240, 109 (2005);
41. (j) G. Smitha, B. Miriyala, and J. S. Williamson, Synlett, 839 (2005);
42. (k) J. S. Yadav, M. Satyanarayana, E. Balanarsaih, and S. Raghavendra, Tetrahedron Lett., 47, 6095 (2006);
43. (l) K. Nagaiah, D. Sreenu, R. S. Rao, G. Vashishta, and J. S. Yadav, Tetrahedron Lett., 47, 4409 (2006);
44. (m) S. R. Kumar and P. Leelavathi, J. Mol. Catal. A, 266, 65 (2007).