Skip to main content
Log in

Transition Metal Substituted Polyoxotungstates in the Catalytic Oxidation of 1H-Indene and 1,2-Dihydronaphthalene with Hydrogen Peroxide

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The oxidation of 1H-indene and 1,2-dihydronaphthalene with hydrogen peroxide in the presence of Mn(III) or Fe(III) substituted Keggin-type polyoxotungstates is described. The products obtained depend on the catalyst and reaction conditions. Ring cleavage was observed, affording dialdehydes under mild and environmentally friendly conditions. Other main products were the α-hydroxy-ketones. The resulting epoxides seem to be intermediates to other oxygenated products.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 3
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Griffith WP (1991) Trans Met Chem 16:548

    Article  CAS  Google Scholar 

  2. Hill CL (1992) In: Strukul G (ed) Catalytic oxidations with hydrogen peroxide as oxidant Ch. 8. Kluwer, Dordrecht

    Google Scholar 

  3. Mizuno N, Misono M (1994) J Mol Catal 86:319

    Article  CAS  Google Scholar 

  4. Okuhara T, Mizuno N, Misono M (1996) Adv Catal 41:113

    Article  CAS  Google Scholar 

  5. Kozhevnikov IV (1998) Chem Rev 98:171

    Article  CAS  Google Scholar 

  6. Vazylyev M, Sloboda-Rozner D, Haimov A, Maayan G, Neumann R (2005) Topics Catal 34:93

    Article  CAS  Google Scholar 

  7. Mizuno N, Yamaguchi K, Kamata K (2005) Coord Chem Rev 249:1944

    Article  CAS  Google Scholar 

  8. Hill CL (2007) J Mol Catal A Chem 262:2

    Article  CAS  Google Scholar 

  9. Kozhevnikov IV (1995) Catal Rev Sci Eng 37:311

    Article  CAS  Google Scholar 

  10. Hill CL, Prosser-McCartha CM (1995) Coord Chem Rev 143:407

    Article  CAS  Google Scholar 

  11. Neumann R (1998) Progr Inorg Chem 47:317

    Article  CAS  Google Scholar 

  12. Simões MMQ, Conceição CMM, Gamelas JAF, Domingues PMDN, Cavaleiro AMV, Cavaleiro JAS, Ferrer-Correia AJV, Johnstone RAW (1999) J Mol Catal A Chem 144:461

    Article  Google Scholar 

  13. Santos ICMS, Simões MMQ, Pereira MMMS, Martins RRL, Neves MGPMS, Cavaleiro JAS, Cavaleiro AMV (2003) J Mol Catal A Chem 195:253

    Article  CAS  Google Scholar 

  14. Santos ICMS, Simões MMQ, Neves MGPMS, Cavaleiro JAS, Cavaleiro AMV (2003) Synlett 1643

  15. Simões MMQ, Santos ICMS, Balula MSS, Gamelas JAF, Cavaleiro AMV, Neves MGPMS, Cavaleiro JAS (2004) Catal Today 91–92:211

    Article  Google Scholar 

  16. Balula MSS, Santos ICMS, Simões MMQ, Neves MGPMS, Cavaleiro JAS, Cavaleiro AMV (2004) J Mol Catal A Chem 222:159

    Article  CAS  Google Scholar 

  17. Cavaleiro AMV (2005) In: Paquette LA (ed) Tungstoboric acid, tetrakis(tetrabutylammonium) Salt, e-EROS encyclopedia of reagents for organic synthesis. Wiley, New York

    Google Scholar 

  18. Santos ICMS, Gamelas JAF, Balula MSS, Simões MMQ, Neves MGPMS, Cavaleiro JAS, Cavaleiro AMV (2007) J Mol Catal A Chem 262:41

    Article  CAS  Google Scholar 

  19. Sanderson WR (2000) Pure Appl Chem 72:1289

    Article  CAS  Google Scholar 

  20. Grigoropoulou G, Clark JH, Elings JA (2003) Green Chem 5:1

    Article  CAS  Google Scholar 

  21. Jones CW (1999) Applications of hydrogen peroxide and derivatives. The Royal Society of Chemistry, Cambridge

    Google Scholar 

  22. Adolfsson H (2004) In: Bäckvall J-E (ed) Modern oxidation methods Ch. 2. Wiley-VCH, Weinheim

    Google Scholar 

  23. Shi Y (2004) In: Bäckvall J-E (ed) Modern oxidation methods Ch. 3. Wiley-VCH, Weinheim

    Google Scholar 

  24. Canali L, Cowan E, Deleuze H, Gibson CL, Sherrington DC (2000) J Chem Soc Perkin Trans 1:2055

    Article  Google Scholar 

  25. Abdi SHR, Kureshy RI, Khan NH, Jasra RV (2004) Catal Surv Asia 8:187

    Article  CAS  Google Scholar 

  26. Kureshy RI, Ahmad I, Khan NH, Abdi SHR, Pathak K, Jasra RV (2006) J Catal 238:134

    Article  CAS  Google Scholar 

  27. Haines AH (1988) Methods for the oxidation of organic compounds. Academic Press, New York, pp 277–292

    Google Scholar 

  28. Hudlický M (1990) Oxidations in organic chemistry. American Chemical Society, Washington

    Google Scholar 

  29. Balula MS, Gamelas JA, Carapuça HM, Cavaleiro AMV, Schlindwein W (2004) Eur J Inorg Chem 619

  30. Rebelo SLH, Simões MMQ, Neves MGPMS, Silva AMS, Tagliatesta P, Cavaleiro JAS (2005) J Mol Catal A Chem 232:135

    Article  CAS  Google Scholar 

  31. Vogel AI (1961) A text-book of quantitative inorganic analysis including elementary instrumental analysis, 3rd edn. Longmans, London

    Google Scholar 

  32. Pedragosa-Moreau S, Archelas A, Furstoss R (1996) Tetrahedron 52:4593

    Article  CAS  Google Scholar 

  33. Palucki M, Finney NF, Pospisil PJ, Güler ML, Ishida T, Jacobsen EN (1998) J Am Chem Soc 120:948

    Article  CAS  Google Scholar 

  34. Choi OK, Cho BT (2001) Tetrahedron Asymmetr 12:903

    Article  CAS  Google Scholar 

  35. Resnick SM, Torok DS, Lee KY, Brand JM, Gibson DT (1994) Appl Environ Microb 60:3323

    CAS  Google Scholar 

  36. Smith K, Liu C-H, El-Hiti GA (2006) Org Biomol Chem 4:917

    Article  CAS  Google Scholar 

  37. Mang H, Gross J, Lara M, Goessler C, Schoemaker HE, Guebitz GM, Kroutil W (2007) Tetrahedron 63:3350

    Article  CAS  Google Scholar 

  38. Chai W, Takeda A, Hara M, Jib S, Horiuchia CA (2005) Tetrahedron 61:2453

    Article  CAS  Google Scholar 

  39. Berglund RA (1995) In: Paquette LA (ed) Encyclopedia of reagents for organic synthesis. Wiley, New York, pp 3837–3843

    Google Scholar 

  40. Dhakshinamoorthy A, Pitchumani K (2006) Tetrahedron 62:9911

    Article  CAS  Google Scholar 

  41. Mang H, Gross J, Lara M, Goessler C, Schoemaker HE, Guebitz GM, Kroutil W (2006) Angew Chem Int Ed 45:5201

    Article  CAS  Google Scholar 

  42. Miyamoto K, Tada N, Ochiai M (2007) J Am Chem Soc 129:2772

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Thanks are due to the University of Aveiro, FCT (Fundação para a Ciência e a Tecnologia) and FEDER for funding the Organic Chemistry Research Unity and CICECO. A.C.E. and I.C.M.S.S. also thank FCT for their grants.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ana M. V. Cavaleiro.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Estrada, A.C., Simões, M.M.Q., Santos, I.C.M.S. et al. Transition Metal Substituted Polyoxotungstates in the Catalytic Oxidation of 1H-Indene and 1,2-Dihydronaphthalene with Hydrogen Peroxide. Catal Lett 128, 281–289 (2009). https://doi.org/10.1007/s10562-008-9718-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-008-9718-8

Keywords

Navigation