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Reactions of Oxiranes and Carbonyl Compounds Catalyzed by Ammonium Decatungstocerate(IV)

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Abstract

Various types of oxiranes react with acetone in the presence of catalytic amounts of ammonium decatungstocerate(IV) icosahydrate, (NH4)8[CeW10O36] ⋅ 20H2O, to give the corresponding 1,3-dioxolanes in excellent yields.

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References

  1. H. T. Green and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd ed. (John Wiley, New York, 1991) pp. 175-198.

    Google Scholar 

  2. P. J. Kocienski, in Protective Groups, Chapter 4, R. Enders, R. Noyori and B. M. Trost (eds) (Thieme, Stuttgart, 1994).

    Google Scholar 

  3. P. A. Gent, J. Chem. Soc. Perkin Trans. 1 (1973) 1858.

    Google Scholar 

  4. D. M. Clod, Chem. Rev. 79 (1979) 491.

    Google Scholar 

  5. J. J. Brown, R. H. Lenhard and S. Brestein, J. Am. Chem. Soc. 86 (1964) 2183.

    Google Scholar 

  6. R. P. Hanzlik and Leinwetter, J. Org. Chem. 43 (1978) 438.

    Google Scholar 

  7. J. Wolinski and A. Czerwinska, Acta Pol. Pharm. 33 (1976) 696.

    Google Scholar 

  8. K. Bruns, J. Conrad and A. Steigel, Tetrahedron 35 (1979) 2523.

    Google Scholar 

  9. F. A. Meskens, Synthesis (1981) 501.

  10. L. W. Zatorski and P. T. Wiezchowski, Catal. Lett. 10 (1991) 211.

    Google Scholar 

  11. H. Steinbrink, Chemische Werke Huls AG, Ger. Pat. (DOS) 1086241, 1959 (Chem. Abstr. 56 (1962) 5969).

    Google Scholar 

  12. A. Gevorkhyan, P. I. Kazarian, O. V. Anakhyan and A. Vardanian, Kim. Geterotsikl. Soedin 1 (1991) 33 (Chem. Abstr. 115 (1991) 8633x).

    Google Scholar 

  13. N. Iranpoor and B. Zeynizadeh, J. Chem. Res. (S) (1998) 466.

  14. N. Iranpoor and F. Kazemi, Synth. Commun. 28 (1998) 3189.

    Google Scholar 

  15. I. Mohammadpoor-Baltork, H. Alian and A. R. Khosropour, Synth. Commun. 31 (2001) 3411.

    Google Scholar 

  16. N. Iranpoor and H. Adibi, Bull. Chem. Soc. Jpn. 73 (2000) 675.

    Google Scholar 

  17. B. Rickborn and R. M. Gerkin, J. Am. Chem. Soc. 93 (1971) 1693.

    Google Scholar 

  18. P. F. Hudrlik, R. N. Misra, G. P. Withers, H. M. Hudrlik, R. J. Rona and J. P. Arcoleo, Tetrahedron Lett. (1976) 1453.

  19. J. Kagan, B. E. Firth, N. Y. Shih and C. Boyajian, J. Org. Chem. 42 (1977) 343.

    Google Scholar 

  20. D. J. Harvey, Res. Commun. Chem. Pathol. Pharmacol. 4 (1972) 247.

    Google Scholar 

  21. D. S. Torok, J. J. Figueroa and W. J. Scott, J. Org. Chem. 58 (1993) 7274.

    Google Scholar 

  22. M. T. Pope, Heteropoly and Isopoly Oxometalates (Springer-Verlag, Berlin, 1983).

    Google Scholar 

  23. M. T. Pope and A. Muller, Angew. Chem., Int. Ed. Engl. 30 (1991) 34.

    Google Scholar 

  24. C. L. Hill and C. M. Prosser-McCartha, Coord. Chem. Rev. 143 (1995) 407.

    Google Scholar 

  25. C. L. Hill, Chem. Rev. 98 (1998) 1.

    Google Scholar 

  26. I. V. Kozhevnikov, Chem. Rev. 98 (1998) 171.

    Google Scholar 

  27. N. Mizuno and M. Misono, J. Mol. Catal. 64 (1990) 1.

    Google Scholar 

  28. N. Mizuno and M. Misono, Chem. Rev. 98 (1998) 199.

    Google Scholar 

  29. T. Okuhara, N. Mizuno and M. Misono, Adv. Catal. 41 (1996) 113.

    Google Scholar 

  30. M. Misono, in Future Opportunities in Catalytic and Engineering Technology, M. Misono, Y. Moro-oka and S. Kimura (eds) (Elsevier, Amsterdam, 1990) p. 13.

    Google Scholar 

  31. Y. Izumi, K. Urabe and M. Onaka, in Zeolite, Clay and Heteropoly Acid in Organic Reactions (Kodansha/VCH, Tokyo, 1992) p. 99.

    Google Scholar 

  32. M. Misono, Catal. Rev. Sci. Eng. 29 (1987) 269.

    Google Scholar 

  33. V. Mirkhani, S. Tangestaninejad and L. Alipanah, Synth. Commun. 32 (2002) 621.

    Google Scholar 

  34. I. V. Kozhevnikov, Catalysts for Fine Chemical Synthesis, Vol. 2 Catalysis by Polyoxometalates (Wiley & Sons, Chichester, UK, 2002).

    Google Scholar 

  35. I. V. Kozhevnikov, I. B. Vasilieva and V. V. Zarutskii, React. Kinet. Catal. Lett. 46 (1992) 107.

    Google Scholar 

  36. R. D. Peacock and T. J. R. Weakley, J. Chem. Soc. A (1971) 1836.

  37. R. Shiozaki, H. Goto and Kera, Bull. Chem. Soc. Jpn. 66 (1993) 2790.

    Google Scholar 

  38. G. H. Posner, Angew. Chem., Int. Ed. Engl. 17 (1978) 487.

    Google Scholar 

  39. D. C. Bailey and S. H. Langer, Chem. Rev. 81 (1981) 109.

    Google Scholar 

  40. P. Laszol, Acc. Chem. Res. 19 (1986) 121.

    Google Scholar 

  41. R. A. Sheldone, I. W. C. E. Arends, G. J. T. Brink and A. Dijksman, Acc. Chem. Res. 35 (2002) 774.

    Google Scholar 

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Authors and Affiliations

  1. Chemistry Department, Isfahan University, Isfahan, 81746-73441, Iran

    V. Mirkhani, S. Tangestaninejad & L. Alipanah

  2. Institute for Advanced Studies in Basic Sciences (IASBS), Gava Zang, Zanjan, 45138-79368, Iran

    B. Yadollahi

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  1. V. Mirkhani
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  2. S. Tangestaninejad
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  3. B. Yadollahi
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  4. L. Alipanah
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Correspondence to V. Mirkhani.

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Mirkhani, V., Tangestaninejad, S., Yadollahi, B. et al. Reactions of Oxiranes and Carbonyl Compounds Catalyzed by Ammonium Decatungstocerate(IV). Catalysis Letters 91, 129–132 (2003). https://doi.org/10.1023/B:CATL.0000006328.46032.a1

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