Catalysis Letters

, Volume 124, Issue 1–2, pp 127–132 | Cite as

Bismuth Subnitrate as an Efficient Heterogeneous Catalyst for Acetalization and Ketalization of Carbonyl Compounds with Diols

  • Shuisheng Wu
  • Weili Dai
  • Shuangfeng Yin
  • Wensheng Li
  • Chak-Tong Au


Bismuth subnitrate has been found to be an excellent catalyst for acetalization and ketalization of a wide range of aldehydes and ketones with diols under mild conditions. The catalyst remained in solid form throughout the reaction and could be readily reused and recycled without any loss of activity. It is deduced that the excellent performance of bismuth subnitrate may be ascribed to its acidity.


Bismuth subnitrate Acetalization Ketalization Carbonyl compound Diol 



This work was financially supported by the National Science Foundation of China (No. 20507005).


  1. 1.
    Suzuki H, Matano Y (2001) Organobismuth chemistry. Elsevier, Amsterdam (References cited therein)Google Scholar
  2. 2.
    Shimada S, Yamazaki O, Tanaka T, Rao MLN, Suzuki Y, Tanaka M (2003) Angew Chem Int Ed 42:1845CrossRefGoogle Scholar
  3. 3.
    Koech PK, Krische MJ (2004) J Am Chem Soc 126:5350CrossRefGoogle Scholar
  4. 4.
    Qin H, Yamagiwa N, Matsunaga S, Shibasaki M (2006) J Am Chem Soc 128:1611CrossRefGoogle Scholar
  5. 5.
    Gagnon A, St-Onge M, Little K, Duplessis M, Barabe F (2007) J Am Chem Soc 129:44CrossRefGoogle Scholar
  6. 6.
    Yin SF, Bao M, Shimada S (2005) In: Michael THL (ed) The 32nd Symposium on Heteroatom Chemistry. Asahi Publishing Company, Tsukuba, p 228Google Scholar
  7. 7.
    Leonard NM, Oswald MC, Freiberg DA, Nattier BA, Smith RC, Mohan RS (2002) J Org Chem 67:5202CrossRefGoogle Scholar
  8. 8.
    Srivastava N, Dasgupta SK, Banik BK (2003) Tetrahedron Lett 44:1191CrossRefGoogle Scholar
  9. 9.
    Greene TW, Wuts PGM (1999) Protective groups in organic synthesis, 2nd edn. Wiley, New YorkGoogle Scholar
  10. 10.
    Bauer K, Garbe D, Surburg H (1990) Common fragrances and flavors materials, 2nd edn. Wiley, New YorkGoogle Scholar
  11. 11.
    Yoshioka S, Oshita M, Tobisu M, Chatani N (2005) Org Lett 7:3697CrossRefGoogle Scholar
  12. 12.
    Wang B, Gu Y, Song G, Yang T, Yang L, Suo J (2005) J Mol Catal A 233:121CrossRefGoogle Scholar
  13. 13.
    Luche JL, Gemal AL (1978) J Chem Soc Chem Commun 976Google Scholar
  14. 14.
    Wang WB, Shi LL, Huang YZ (1990) Tetrahedron 46:3315CrossRefGoogle Scholar
  15. 15.
    Firouzabadi H, Iranpoor N, Kamiri B (1999) Synth Commun 29:2255CrossRefGoogle Scholar
  16. 16.
    Velusamy S, Punniyamurthy T (2004) Tetrahedron Lett 45:4917CrossRefGoogle Scholar
  17. 17.
    Smith BM, Graham AE (2006) Tetrahedron Lett 47:9317CrossRefGoogle Scholar
  18. 18.
    Sueiue M, Venanzi LM (2001) Helv Chem Acta 84:898CrossRefGoogle Scholar
  19. 19.
    Duan Z, Gu Y, Deng Y (2006) Catal Commun 7:651CrossRefGoogle Scholar
  20. 20.
    Kim YJ, Varma RS (2005) Tetrahedron Lett 46:7447CrossRefGoogle Scholar
  21. 21.
    Gupta N, Sonu, Kad GL, Singh J (2007) Catal Commun 8:1323Google Scholar
  22. 22.
    Sugimura R, Qiao K, Tomida D, Yokoyama C (2007) Catal Commun 8:770CrossRefGoogle Scholar
  23. 23.
    Robinson MWC, Graham AE (2007) Tetrahedron Lett 48:4727CrossRefGoogle Scholar
  24. 24.
    Jermy BR, Pandurangan A (2006) J Mol Catal A 256:184CrossRefGoogle Scholar
  25. 25.
    Srivastava P, Srivastava R (2007) Catal Commun. doi: 10.1016/j.catcom.2007.07.008
  26. 26.
    Thomas B, Prathapan S, Sugunan S (2005) Micropor Mesopor Mater 80:65CrossRefGoogle Scholar
  27. 27.
    Thomas B, Prathapan S, Sugunan S (2004) Appl Catal A 277:247CrossRefGoogle Scholar
  28. 28.
    Climent MJ, Corma A, Velty A (2004) Appl Catal A 263:155CrossRefGoogle Scholar
  29. 29.
    Capeletti MR, Balzano L, de la Puente G, Laborde M, Sedran U (2000) Appl Catal A 198:L1CrossRefGoogle Scholar
  30. 30.
    Ribeiro NM, Pinto AC, da Silva BV, Violante FA, Dias MO (2007) Catal Commun 8:2130CrossRefGoogle Scholar
  31. 31.
    Chopade SP (1999) React Funct Polym 42:201CrossRefGoogle Scholar
  32. 32.
    Jermy BR, Pandurangan A (2006) Catal Commun 7:921CrossRefGoogle Scholar
  33. 33.
    Jermy BR, Pandurangan A (2005) Appl Catal A 295:185CrossRefGoogle Scholar
  34. 34.
    Wang X, Cheng S, Chan JCC, Chao JCH (2006) Micropor Mesopor Mater 96:321CrossRefGoogle Scholar
  35. 35.
    Palaniappan S, Narender P, Saravanan C, Rao V-J (2003) Synlett 12:1793CrossRefGoogle Scholar
  36. 36.
    Shimizu K, Hayashi E, Hatamachi T, Kodama T, Higuchi T, Satsuma A, Kitayama Y (2005) J Catal 231:131CrossRefGoogle Scholar
  37. 37.
    Ledneczkia I, Darányi M, Fülöp F, Molnár Á (2005) Catal Today 100:437CrossRefGoogle Scholar
  38. 38.
    Shimizu K, Hayashi E, Hatamachi T, Kodama T, Kitayama Y (2004) Tetrahedron Lett 45:5135CrossRefGoogle Scholar
  39. 39.
    Mirjalili BBF, Zolfigol MA, Bamoniri A, Hazar A (2004) Bull Korean Chem Soc 25:865CrossRefGoogle Scholar
  40. 40.
    Patel SM, Chudasama UV, Ganeshpure PA (2003) J Mol Catal A 194:267CrossRefGoogle Scholar
  41. 41.
    Niu MJ (2006) Chem World (in Chinese) 626 (References therein)Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2008

Authors and Affiliations

  1. 1.College of Chemistry and Chemical EngineeringHunan UniversityChangshaChina
  2. 2.Department of ChemistryHong Kong Baptist UniversityHong KongChina

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