Skip to main content
Log in

Peroxidation of β-diketones and β-keto esters with tert-butyl hydroperoxide in the presence of Cu(ClO4)2/SiO2

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Reactions of β-diketones and β-keto esters with tert-butyl hydroperoxide under heterogeneous conditions using SiO2-supported copper(II) perchlorate as a catalyst give rise to α-peroxidation products in 65—82% yields. A possibility to reuse the catalyst was demonstrated.

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.

Similar content being viewed by others

References

  1. Organic Peroxides, Ed. W. Ando, Wiley, New York, 1992, 861 pp.

  2. Peroxide Chemistry, Ed. W. Adam, Wiley-VCH, New York, 2000, 664 pp.

  3. E. T. Denisov, T. G. Denisova, T. S. Pokidova, Handbook of Free Radical Initiators, John Wiley and Sons, Inc., 2005, 904 pp.

    Google Scholar 

  4. A. Bunge, H.-J. Hamann, J. Liebscher, Tetrahedron Lett., 2009, 50, 524–526

    CAS  Google Scholar 

  5. B. Das, B. Veeranjaneyulu, M. Krishnaiah, P. Balasubramanyam, J. Mol. Catal., A, 2008, 284, 116–119

    CAS  Google Scholar 

  6. P. Ghorai, P. H. Dussault, Org. Lett., 2008, 10, 4577–4579

    CAS  Google Scholar 

  7. A. O. Terent´ev, M. M. Platonov, Yu. N. Ogibin, G. I. Nikishin, Synth. Commun., 2007, 37, 1281–1287

    Google Scholar 

  8. A. O. Terent´ev, M. M. Platonov, A. V. Kutkin, Cent. Europ. J. Chem., 2006, 4, 207–215

    Google Scholar 

  9. D. Azarifar, K. Khosravi, F. Soleimanei, Synthesis, 2009, 2553–2556

    Google Scholar 

  10. P. Ghorai, P. H. Dussault, Org. Lett., 2009, 11, 213–216

    CAS  Google Scholar 

  11. A. O. Terent´ev, A. V. Kutkin, Z. A. Starikova, M. Yu. Antipin, Yu. N. Ogibin, G. I. Nikishin, Synthesis, 2004, 2356–2366

    Google Scholar 

  12. A. G. Griesbeck, D. Blunk, T. El-Idreesy, A. Raabe, Angew. Chem., Int. Ed., 2007, 46, 8883–8886

    CAS  Google Scholar 

  13. A. O. Terent´ev, M. M. Platonov, I. B. Krylov, V. V. Chernyshev, G. I. Nikishin, Org. Biomol. Chem., 2008, 6, 4435–4441

    Google Scholar 

  14. A. O. Terent´ev, A. V. Kutkin, N. A. Troizky, Yu. N. Ogibin, G. I. Nikishin, Synthesis, 2005, 2215–2219

    Google Scholar 

  15. M. Ravi, D. Anand, R. Maurya, P. Chauhan, N. K. Naikade, S. K. Shukla, P. P. Yadav, Synlett, 2013, 24, 173–176

    CAS  Google Scholar 

  16. A. Bartoschek, T. T. El-Idreesy, A. G. Griesbeck, L.-O. Hoeinck, J. Lex, C. Miara, J. M. Neudoerfl, Synthesis, 2005, 2433–2444

    Google Scholar 

  17. B. A. Šolaja, N. Terzic, G. Pocsfalvi, L. Gerena, B. Tinant, D. Opsenica, W. K. Milhous, J. Med. Chem., 2002, 45, 3331–3336.

    Google Scholar 

  18. C. W. Jefford, Curr. Top. Med. Chem., 2012, 12, 373–399

    CAS  Google Scholar 

  19. D. M. Opsenica, B. A. Šolaja, J. Serb. Chem. Soc., 2009, 74, 1155–1193

    CAS  Google Scholar 

  20. P. Ghorai, P. H. Dussault, C. Hu, Org. Lett., 2008, 10, 2401–2404

    CAS  Google Scholar 

  21. J. L. Vennerstrom, H.-N. Fu, W. Y. Ellis, A. L. Ager, J. K. Wood, S. L. Andersen, L. Gerena, W. K. Milhous, J. Med. Chem., 1992, 35, 3023–3027

    CAS  Google Scholar 

  22. N. Yadav, C. Sharma, S. K. Awasthi, RSC Adv., 2014, 4, 5469–5498

    CAS  Google Scholar 

  23. A. O. Terent´ev, D. A. Borisov, I. A. Yaremenko, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 48, 55–58 [Khim. Geterotsikl. Soedin., 2012, 60–63]

    Google Scholar 

  24. H. D. Hao, S. Wittlin, Y. Wu, Chem. Eur. J., 2013, 19, 7605–7619

    CAS  Google Scholar 

  25. Y. Li, H.-D. Hao, S. Wittlin, Y. Wu, Chem. Asian. J., 2012, 7, 1881–1886.

    CAS  Google Scholar 

  26. J. Boissier, J. Portela, V. Pradines, F. Cosledan, A. Robert, B. Meunier, C. R. Chim., 2012, 15, 75–78

    CAS  Google Scholar 

  27. J. Keiser, V. Veneziano, L. Rinaldi, L. Mezzino, U. Duthaler, G. Cringoli, Res. Vet. Sci., 2010, 88, 107–110

    CAS  Google Scholar 

  28. K. Ingram, I. A. Yaremenko, I. B. Krylov, L. Hofer, A. O. Terent´ev, J. Keiser, J. Med. Chem., 2012, 55, 8700–8711.

    CAS  Google Scholar 

  29. N. Kumar, M. Sharma, D. S. Rawat, Curr. Med. Chem., 2011, 18, 3889–3928

    CAS  Google Scholar 

  30. Z. Juranic´, D. Opsenica, B. A. Šolaja, Invest. New Drugs, 2009, 27, 432–439

    Google Scholar 

  31. N. Terzic´, D. Opsenica, D. Milic´, B. Tinant, K. S. Smith, W. K. Milhous, B. A. Šolaja, J. Med. Chem., 2007, 50, 5118–5127.

    Google Scholar 

  32. R. Matyáš, P. Juí, Primary Explosives, Springer Heidelberg—New York—Dordrecht—London, 2013, 338 pp.

  33. J. Chen, W. Wu, A. J. McNeil, Chem. Commun., 2012, 48, 7310–7312

    CAS  Google Scholar 

  34. K. B. Landenberger, O. Bolton, A. J. Matzger, Angew. Chem., Int. Ed., 2013, 52, 6468–6471

    CAS  Google Scholar 

  35. R. Matyáš, R. Jirásko, A. Ly ka, J. Pachmán, Propellants Explos. Pyrotech., 2011, 36, 219–224

    Google Scholar 

  36. H. Östmark, S. Wallin, H. G. Ang, Propellants Explos. Pyrotech., 2012, 37, 12–23

    Google Scholar 

  37. A. O. Terent´ev, M. M. Platonov, E. J. Sonneveld, R. Peschar, V. V. Chernyshev, Z. A. Starikova, G. I. Nikishin, J. Org. Chem., 2007, 72, 7237–7243.

    Google Scholar 

  38. Y. Li, H.-D. Hao, Q. Zhang, Y. Wu, Org. Lett., 2009, 11, 1615–1618

    CAS  Google Scholar 

  39. B. Das, M. Krishnaiah, B. Veeranjaneyulu, B. Ravikanth, Tetrahedron Lett., 2007, 48, 6286–6289

    CAS  Google Scholar 

  40. P. Ghorai, P. H. Dussault, Org. Lett., 2008, 10, 4577–4579

    CAS  Google Scholar 

  41. A. O. Terent´ev, M. M. Platonov, A. S. Kashin, G. I. Nikishin, Tetrahedron, 2008, 64, 7944–7948

    Google Scholar 

  42. A. O. Terent´ev, A. V. Kutkin, M. M. Platonov, Yu. N. Ogibin, G. I. Nikishin, Tetrahedron Lett., 2003, 44, 7359–7363

    Google Scholar 

  43. A. G. Griesbeck, T. T. El-Idreesy, L.-O. Hoeinck, J. Lex, R. Brun, Bioorg. Med. Chem. Lett., 2005, 15, 595–597

    CAS  Google Scholar 

  44. J. F. B. Hall, R. A. Bourne, X. Han, J. H. Earley, M. Poliakoff, M. W. George, Green Chem., 2013, 15, 177–180

    CAS  Google Scholar 

  45. A. Bunge, H.-J. Hamann, J. Liebscher, Tetrahedron Lett., 2009, 50, 524–526

    CAS  Google Scholar 

  46. B. Das, B. Veeranjaneyulu, M. Krishnaiah, P. Balasubramanyam, J. Mol. Catal., A, 2008, 284, 116–119

    CAS  Google Scholar 

  47. D. Azarifar, K. Khosravi, F. Soleimanei, Synthesis, 2009, 2553–2556

    Google Scholar 

  48. S. Pramanik, P. Ghorai, Org. Lett., 2013, 15, 3832–3835

    CAS  Google Scholar 

  49. A. G. Griesbeck, V. Schlundt, J. M. Neudoerfl, RSC Adv., 2013, 3, 7265–7270

    CAS  Google Scholar 

  50. M. Ravi, D. Anand, R. Maurya, P. Chauhan, N. K. Naikade, S. K. Shukla, P. P. Yadav, Synlett, 2013, 24, 173–176

    CAS  Google Scholar 

  51. A. Bartoschek, T. T. El-Idreesy, A. G. Griesbeck, L.-O. Hoeinck, J. Lex, C. Miara, J. M. Neudoerfl, Synthesis, 2005, 2433–2444

    Google Scholar 

  52. A. Rieche, C. Bischoff, Chem. Ber., 1962, 95, 77–82

    CAS  Google Scholar 

  53. N. A. Milas, O. L. Mageli, A. Golubovic, R. W. Arndt, J. C. J. Ho, J. Am. Chem. Soc., 1963, 85, 222–226

    CAS  Google Scholar 

  54. A. O. Terent´ev, D. A. Borisov, V. A. Vil´, V. M. Dembitsky, Beilstein J. Org. Chem., 2014, 10, 34–114

    Google Scholar 

  55. A. O. Terent´ev, D. A. Borisov, V. V. Semenov, V. V. Chernyshev, V. M. Dembitsky, G. I. Nikishin, Synthesis, 2011, 2091–2100.

    Google Scholar 

  56. A. O. Terent´ev, D. A. Borisov, V. V. Chernyshev, G. I. Nikishin, J. Org. Chem., 2009, 74, 3335–3340

    Google Scholar 

  57. A. O. Terent´ev, D. A. Borisov, I. A. Yaremenko, V. V. Chernyshev, G. I. Nikishin, J. Org.Chem., 2010, 75, 5065–5071

    Google Scholar 

  58. I. A. Yaremenko, A. O. Terent´ev, V. A. Vil´, R. A. Novikov, V. V. Chernyshev, V. A. Tafeenko, D. O. Levitsky, F. Fleury, G. I. Nikishin, Chem. Eur. J., 2014, 20, 1016–10169

    Google Scholar 

  59. A. O. Terent´ev, I. A. Yaremenko, V. A. Vil´, I. K. Moiseev, S. A. Kon´kov, V. M. Dembitsky, D. O. Levitsky, G. I. Nikishin, Org. Biomol. Chem., 2013, 11, 2613–2623

    Google Scholar 

  60. A. O. Terent´ev, I. A. Yaremenko, V. A. Vil´, V. M. Dembitsky, G. I. Nikishin, Synthesis, 2013, 45, 246–250.

    Google Scholar 

  61. M. S. Kharasch, P. Pauson, W. Nudenberg, J. Org. Chem., 1953, 18, 322–327

    CAS  Google Scholar 

  62. M. S. Kharasch, A. Fono, J. Org. Chem., 1958, 23, 324–325

    Google Scholar 

  63. M. S. Kharasch, A. Fono, J. Org. Chem., 1959, 24, 72–78.

    CAS  Google Scholar 

  64. G. B. Shul´pin, J. Gradinaru, Y. N. Kozlov, Org. Biomol. Chem., 2003, 1, 3611–3617

    Google Scholar 

  65. S. Araneo, F. Fontana, F. Minisci, F. Recupero, A. Serri, J. Chem. Soc., Chem. Commun., 1995, 1399–1400

    Google Scholar 

  66. A. Bravo, H.-R. Bjørsvik, F. Fontana, L. Liguori, F. Minisci, J. Org. Chem., 1997, 62, 3849–3857

    CAS  Google Scholar 

  67. M. B. Meder, L. H. Gade, Eur. J. Inorg. Chem., 2004, 22716–22722

    Google Scholar 

  68. T. Punniyamurthy, L. Rout, Coord. Chem. Rev., 2008, 252, 134–154.

    CAS  Google Scholar 

  69. W. Treibs, G. Pellmann, Chem. Ber., 1954, 87, 1201–1205

    CAS  Google Scholar 

  70. L. Saussine, E. Brazi, A. Robine, H. Mimoun, J. Fischer, R. Weiss, J. Am. Chem. Soc., 1985, 107, 3534–3540.

    CAS  Google Scholar 

  71. R. A. Leising, Y. Zang, L. Que, Jr., J. Am. Chem. Soc., 1991, 113, 8555–8557

    CAS  Google Scholar 

  72. T. Kojima, R. A. Leising, S. Yan, L. Que, Jr., J. Am. Chem. Soc., 1993, 115, 1132–1135

    Google Scholar 

  73. I. W. C. E. Arends, K. U. Ingold, D. D. M. Wayner, J. Am. Chem. Soc., 1995, 117, 4710–4711

    CAS  Google Scholar 

  74. W. Liu, Y. Li, K. Liu, Z. Li, J. Am. Chem. Soc., 2011, 133, 1075–1075.

    Google Scholar 

  75. F. Minisci, F. Fontana, S. Araneo, F. Recupero, J. Chem. Soc., Chem. Commun., 1994, 1823–1824.

    Google Scholar 

  76. M. T. Rispens, O. J. Gelling, A. M. de Vries, A. Meetsma, F. van Bolhuis, B. L. Feringa, Tetrahedron, 1996, 52, 3521–3546.

    CAS  Google Scholar 

  77. J. Q. Yu, E. J. Corey, Org. Lett., 2002, 4, 2727–2730.

    CAS  Google Scholar 

  78. T. Nishimura, T. Onoue, K. Ohe, J. I. Tateiwa, S. Uemura, Tetrahedron Lett., 1998, 39, 4359–4362.

    CAS  Google Scholar 

  79. S.-I. Murahashi, D. Zhang, Chem. Soc. Rev., 2008, 37, 1490–1501

    CAS  Google Scholar 

  80. S.-I. Murahashi, T. Naota, T. Kuwabara, T. Saito, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc., 1990, 112, 7820–7822

    CAS  Google Scholar 

  81. S.-I. Murahashi, T. Naota, K. Yonemura, J. Am. Chem. Soc., 1988, 110, 8256–8258.

    CAS  Google Scholar 

  82. M. Yoshioka, T. Nishioka, T. Hasegawa, J. Org. Chem., 1993, 58, 278–281.

    CAS  Google Scholar 

  83. J. Christoffers, T.Werner, W. Frey, A. Baro, Eur. J. Org. Chem., 2003, 4879–4886.

    Google Scholar 

  84. M. T. Rahman, H. Nishino, Org. Lett., 2003, 5, 2887–2890.

    CAS  Google Scholar 

  85. G. Bianchi, F. Mazza, T. Mussini, Electrochim. Acta, 1962, 7, 457–473

    CAS  Google Scholar 

  86. K. Goszner, H. Bischof, J. Catal., 1974, 32, 175–182

    CAS  Google Scholar 

  87. J. Weiss, Trans. Faraday Soc., 1935, 31, 1547–1557

    CAS  Google Scholar 

  88. D. B. Broughton, R. L. Wentworth, J. Am. Chem. Soc., 1947, 69, 741–744

    CAS  Google Scholar 

  89. S.-H. Do, B. Batchelor, H.-K. Lee, S.-H. Kong, Chemosphere, 2009, 75, 8–12

    CAS  Google Scholar 

  90. M. A. Hasan, M. I. Zaki, L. Pasupulety, K. Kumari, Appl. Catal., A, 1999, 181, 171–179

    CAS  Google Scholar 

  91. Y. Yang, A. C. C. Tseung, Z. G. Lin, J. Electroanal. Chem., 1994, 370, 159–164.

    CAS  Google Scholar 

  92. G. I. Nikishin, A. V. Aleksandrov, A. V. Ignatenko, E. K. Starostin, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1984, 33, 2407–2409 [Izv. Akad. Nauk SSSR, Ser. Khim., 1984, 2628–2630]

    Google Scholar 

  93. G. P. Chiusoli, F. Minisci, Gazz. Chim. Ital., 1958, 88, 261–268

    CAS  Google Scholar 

  94. F. Minisci, A. Portolani, Gazz. Chim. Ital., 1959, 89, 1922–1937

    CAS  Google Scholar 

  95. J. B. Braunwarth, G. W. Crosby, J. Org. Chem., 1962, 27, 2064–2067

    CAS  Google Scholar 

  96. Yu. N. Ogibin, E. K. Starostin, A. V. Aleksandrov, K. K. Pivnitsky, G. I. Nikishin, Synthesis, 1994, 901–903

    Google Scholar 

  97. O. Blank, N. Raschke, M. R. Heinrich, Tetrahedron Lett., 2010, 51, 1758–1760

    CAS  Google Scholar 

  98. A. Prechter, M. R. Heinrich, Synthesis, 2011, 1515–1525

    Google Scholar 

  99. K. J. McCullough, Yu. Motomura, A. Masuyama, M. Nojima, Chem. Commun., 1998, 1173

    Google Scholar 

  100. Yu. N. Ogibin, A. O. Terent´ev, V. P. Ananikov, G. I. Nikishin, Russ. Chem. Bull. (Int. Ed.), 2001, 50, 2149–2155 [Izv. Akad. Nauk SSSR, Ser. Khim., 2001, 2052—2057]

    CAS  Google Scholar 

  101. H. E. B. Lempers, R. A. Sheldon, K. A. D. Swift, Chem. Lett., 2002, 830–831

    Google Scholar 

  102. A. Masuyama, T. Sugawara, M. Nojima, K. J. McCullough, Tetrahedron, 2003, 53, 353–366.

    Google Scholar 

  103. A. S. Kashin, V. P. Ananikov, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 2602–2607 [Izv. Akad. Nauk, Ser. Khim., 2011, 2551—2556].

    CAS  Google Scholar 

  104. M. Ringuet, D. Girard, C. Chapados, Can. J. Chem., 1991, 69, 1070–1079.

    CAS  Google Scholar 

  105. D. Kalaitzakis, J. D. Rozzell, I. Smonou, S. Kambourakis, Adv. Synth. Catal., 2006, 348, 1958–1969.

    CAS  Google Scholar 

  106. R. W. Kluiber, F. Oberender, C. Rossi, J. Org. Chem., 1960, 25, 1069–1070.

    CAS  Google Scholar 

  107. S. Brooker, J. Olguin, New J. Chem., 2011, 35, 1242–1253.

    Google Scholar 

  108. T. Sakai, K. Miyata, S. Tsuboi, M. Utaka, Bull. Chem. Soc. Jpn., 1989, 62, 4072–4074.

    CAS  Google Scholar 

  109. W. B. Renfrow, A. A. Renfrow, J. Am. Chem. Soc., 1946, 68, 1801–1804.

    CAS  Google Scholar 

  110. N. F. Albertson, J. Am. Chem. Soc., 1950, 72, 2594–2599.

    CAS  Google Scholar 

  111. V. A. Martin, D. H. Murray, N. E. Pratt, Y.-B. Zhao, K. F. Albizati, J. Am. Chem. Soc., 1990, 112, 6965–6978.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. O. Terent´ev.

Additional information

Dedicated to Academician of the Russian Academy of Sciences Yu. N. Bubnov on the occasion of his 80th birthday and to the 60th anniversary of the foundation of A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2461—2466, November, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Terent´ev, A.O., Vil´, V.A., Bityukov, O.V. et al. Peroxidation of β-diketones and β-keto esters with tert-butyl hydroperoxide in the presence of Cu(ClO4)2/SiO2 . Russ Chem Bull 63, 2461–2466 (2014). https://doi.org/10.1007/s11172-014-0763-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-014-0763-8

Keywords

Navigation