Skip to main content
Log in

Transformations of Peroxide Products of Alkene Ozonolysis

  • Review
  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The review summarizes the data published over the past decade on the transformations of peroxide products of alkene ozonolysis, such as cleavage reactions and reactions with reducing agents and nitrogen-containing compounds, as well as on the use of these transformations in directed syntheses.

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. Zvereva, T.I., Kukovinets, O.S., Kasradze, V.G., and Kazakova, O.B., Russ. J. Org. Chem., 2010, vol. 46, no. 10, p. 1431.

    Article  CAS  Google Scholar 

  2. Ishmuratov, G.Yu., Legostaeva, Yu.V., Botsman, L.P., and Tolstikov, G.A., Russ. J. Org. Chem., 2010, vol. 46, no. 11, p. 1593.

    Article  CAS  Google Scholar 

  3. Van Ornum, S.G., Champeau, R.M., and Pariza, R., Chem. Rev, 2006, vol. 106, p. 2990.

    Article  CAS  PubMed  Google Scholar 

  4. Kukovinets, O.S., Zvereva, T.I., Kabalnova, N.N., Kasradze, V.G., Salimova, E.V., Khalitova, L.R., Abdullin, M.I., and Spirikhin, L.V., Mendeleev Commun, 2009, vol. 19, p. 106.

    Article  CAS  Google Scholar 

  5. Schiaffo, C.E. and Dussault, P.H., J. Org. Chem., 2008, vol. 73, p. 4688.

    Article  CAS  PubMed  Google Scholar 

  6. Suwancharoen, S., Pornpakakul, S., and Muangsin, N., Tetrahedron Lett., 2012, vol. 53, p. 5418.

    Article  CAS  Google Scholar 

  7. Ishmuratov, G.Yu., Legostaeva, Yu.V., Botsman, L.P., Nasibullina, G.V., Muslukhov, R.R., Kazakov, D.V., and Tolstikov, G.A., Russ. J. Org. Chem., 2012, vol. 48, no. 1, p. 18.

    Article  CAS  Google Scholar 

  8. Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Botsman, L.P., Muslukhov, R.R., and Tolstikov, G.A., Russ. J. Org. Chem., 2014, 50, vol. 12, p. 1746.

    Article  CAS  Google Scholar 

  9. Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Muslukhov, R.R., Botsman, L.P., and Kozlova, G.G., Chem. Nat. Compd., 2015, vol. 51, no. 1, p. 71.

    Article  CAS  Google Scholar 

  10. Raskil’dina, G.Z., Legostaeva, Yu.V., Garifullina, L.R., Sultanova, R.M., Ishmuratov, G.Yu., and Zlotskii, S.S., Dokl. Chem., 2015, vol. 462, no. 1, p. 127.

    Article  CAS  Google Scholar 

  11. Yadav, J.S., Krishna, V.H., Srilatha, A., Somaiah, R., and Subba Reddy, B.V., Synthesis, 2010, no. 17, p. 3004.

    Google Scholar 

  12. Fisher, T.J. and Dussault, P.H., Tetrahedron Lett., 2010, vol. 51, p. 5615.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Amarante, G.W., Synlett, 2009, no. 1, p. 155.

    Google Scholar 

  14. Cheng, P., Shao, W., and Clive, D.L.J., J. Org. Chem., 2013, vol. 78, no. 23, p. 11860.

    Article  CAS  PubMed  Google Scholar 

  15. Schneider, M.-A., Dötterl, S., and Siefert, K., Chem. Biodiversity, 2013, vol. 10, p. 1252.

    Article  CAS  Google Scholar 

  16. Hoegenauer, E.K. and Thomas, E.J., Org. Biomol. Chem., 2012, vol. 10, p. 6995.

    Article  CAS  PubMed  Google Scholar 

  17. Pearson, A.J., Kim, E.H., and Sun, H., Tetrahedron, 2010, vol. 66, p. 4943.

    Article  CAS  Google Scholar 

  18. Kulkarni, M.G., Dhondge, A.P., Borhade, A.S., Gaikwad, D.D., Chavhan, S.W., Shaikh, Y.B., Nigdale, V.B., Desai, M.P., Birhade, D.R., and Shinde, M.P., Eur. J. Org. Chem., 2009, p. 3875.

    Google Scholar 

  19. Tian, W.-S., Dung, K., Sun, Y.-S., Chen, L., and Lei, Z., Synthesis, 2013, vol. 45, p. 438.

    Article  CAS  Google Scholar 

  20. Yadav, J.S., Krishana, G.C., and Kumar, S.N., Tetrahedron, 2010, vol. 66, p. 480.

    Article  CAS  Google Scholar 

  21. Perlikowska, W. and Mikolajczyk, M., Tetrahedron: Asymmetry, 2011, vol. 22, p. 1767.

    Article  CAS  Google Scholar 

  22. Strikrishna, A. and Gowri, V., Synlett, 2011, no. 18, p. 2652.

    Google Scholar 

  23. Chavan, S.P., Lasonkar, P.B., and Chavan, P.N., Tetrahedron: Asymmetry, 2013, vol. 24, p. 1473.

    Article  CAS  Google Scholar 

  24. Ren, L. and Piers, E., Tetrahedron Lett., 2012, vol. 53, p. 3329.

    Article  CAS  Google Scholar 

  25. Giesbrecht, H.E., Knight, B.J., Tanguileg, N.R., Emerson, C.R., and Blakemore, P.R., Synlett, 2010, no. 3, p. 374.

    Google Scholar 

  26. Ishmuratov, G.Yu., Yakovleva, M.P., Shutova, M.A., Muslukhov, R.R., Ishmuratova, N.M., and Tolstikov, G.A., Chem. Nat. Compd., 2014, vol. 50, no. 4, p. 658.

    Article  CAS  Google Scholar 

  27. Paioti, P.H.S., Rezende, P., and Coelho, F., J. Braz. Chem. Soc., 2012, vol. 23, no. 2, p. 285.

    Article  CAS  Google Scholar 

  28. Hilt, G., Arndt, M., and Weske, D.F., Synthesis, 2010, no. 8, p. 1321.

    Google Scholar 

  29. Hilt, G., Synlett, 2011, no. 12, p. 1654.

    Google Scholar 

  30. Heo, G.S., Cho, S., and Wooley, K.L., Polym. Chem., 2014, vol. 5, p. 3555.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. Reynaud, S., Giorgi, M., Doucet, H., and Santelli, M., Tetrahedron, 2010, vol. 66, p. 4101.

    Article  CAS  Google Scholar 

  32. Reynaud, S., Giorgi, M., Doucet, H., and Santelli, M., Tetrahedron Lett., 2009, vol. 50, p. 3385.

    Article  CAS  Google Scholar 

  33. Zhylitskaya, H., Litvinovskaya, R., Drach, S., and Khripach, V., Tetrahedron Lett., 2011, vol. 52, p. 5267.

    Article  CAS  Google Scholar 

  34. Budaev, A.S., Mikhailova, R.L., Spirikhin, L.V., and Baltina, L.A., Chem. Nat. Compd., 2016, vol. 52, no. 3, p. 448.

    Article  CAS  Google Scholar 

  35. Budaev, A.S., Mikhailova, L.R., Spirikhin, L.V., and Baltina, L.A., Chem. Nat. Compd., 2014, vol. 50, no. 2, p. 302.

    Article  CAS  Google Scholar 

  36. Laventin, D.M., Davies, M., Evinson, E.L., Jenkins, P.R., Cullins, P.M., and Garcia, M.D., Tetrahedron, 2009, vol. 65, p. 4766.

    Article  CAS  Google Scholar 

  37. Dalby, S.M., Goodwin-Tindall, J., and Paterson, I., Angew. Chem., Int. Ed., 2013, vol. 52, p. 6517.

    Article  CAS  Google Scholar 

  38. Ho, S., Bucher, C., and Leighton, J.L., Angew. Chem., Int. Ed., 2013, vol. 52, p. 6757.

    Article  CAS  Google Scholar 

  39. Florence, G.J., Morris, J.C., Murrey, R.G., Vanga, R.R., Osler, J.D., and Smith, T.K., Chem. Eur. J., 2013, vol. 19, p. 8309.

    Article  CAS  PubMed  Google Scholar 

  40. Aldrich, L.N., Berry, C.B., Bates, B.S., Koncol, L.C., So, M., and Lindsley, C.W., Eur. J. Org. Chem., 2013, p. 4215.

    Google Scholar 

  41. Zhan, W., Jiang, Y., Sharma, S., Brodie, P.J., Bane, S., Kingston, D.G.I., Liotta, D.C., and Snyder, J.P., Chem. Eur. J., 2011, vol. 17, p. 14792.

    Article  CAS  PubMed  Google Scholar 

  42. Holmes, M.T. and Britton, R., Chem. Eur. J., 2013, vol. 19, p. 12649.

    Article  CAS  PubMed  Google Scholar 

  43. Miege, F., Meyer, C., and Cossy, J., Chem. Eur. J., 2012, vol. 18, p. 7810.

    Article  CAS  PubMed  Google Scholar 

  44. Tietze, L.F., Biller, S., and Wolfram, T., Synlett, 2010, no. 14, p. 2130.

    Google Scholar 

  45. Bielitza, M. and Pietruszka, J., Chem. Eur. J., 2013, vol. 19, p. 8300.

    Article  CAS  PubMed  Google Scholar 

  46. Kosaki, Y., Ogawa, N., and Kobayashi, Y., Tetrahedron Lett., 2010, vol. 51, p. 1856.

    Article  CAS  Google Scholar 

  47. LaPorte, M.G., Tsegay, S., Hong, K.B., Lu, C., Fang, C., Wang, L., Xie, X.-Q., and Floreancig, P.E., ACS Comb. Sci., 2013, vol. 15, p. 344.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  48. Kumar, K.S.A., Rathee, J.S., Subramanian, M., and Chattopadhayay, S., J.Org. Chem., 2013, vol. 78, no. 15, p. 7406.

    Article  CAS  PubMed  Google Scholar 

  49. Roydhouse, M.D., Motherwell, W.B., Constantinou, A., Gavriilidis, A., Wheeler, R., Down, K., and Campbell, I., RSC Adv., 2013, vol. 3, p. 5076.

    Article  CAS  Google Scholar 

  50. Lewis, K., Vivier, L., Clacens, J.-M., Brandhorst, M., Dubois, J.-L, De Oliveira Vigier, K., and Pouilloux, Y., Green Chem., 2014, vol. 16, p. 96.

    Article  Google Scholar 

  51. Kersten, L. and Hilt, G., Adv. Synth. Catal, 2012, vol. 354, p. 863.

    Article  CAS  Google Scholar 

  52. Edvinsson, S., Johansson, S., and Larsson, A., Tetrahedron Lett., 2012, vol. 53, p. 6819.

    Article  CAS  Google Scholar 

  53. Smits, G. and Zemribo, R., Org. Lett., 2013, vol. 15, no. 17, p. 4406.

    Article  CAS  PubMed  Google Scholar 

  54. Debnar, T., Wang, T., and Menche, D., Org. Lett., 2013, vol. 15, no. 11, p. 2774.

    Article  CAS  PubMed  Google Scholar 

  55. Luna-Freire, K.R., Scaramal, J.P.S., Resende, J.A.L.C., Tormena, C.F., Oliveira, F.L., Aparicio, R., and Coelho, F., Tetrahedron, 2014, vol. 70, p. 3319.

    Article  CAS  Google Scholar 

  56. Guduguntla, S., Faňanás-Mastal, M., and Feringa, B.L., J. Org. Chem., 2013, vol. 78, no. 17, p. 8274.

    Article  CAS  PubMed  Google Scholar 

  57. Iskakova, M.M., Biktagirov, I.M., Faizullina, L.Kh., Salikhov, Sh.M., Safarov, M.G., and Valeev, F.A., Russ. J. Org. Chem., 2014, vol. 50, no. 1, p. 105.

    Article  CAS  Google Scholar 

  58. Lentsch, C., Fürst, R., Muzler, J., and Rinner, U., Eur. J. Org. Chem., 2014, p. 919.

    Google Scholar 

  59. Reynaud, C., Doucet, H., and Santelli, M., Synthesis, 2010, no. 11, p. 1787.

    Google Scholar 

  60. Pujol, A.R., Ratel-Ramond, N., and Gourdon, A., Tetrahedron, 2013, vol. 69, p. 9139.

    Article  CAS  Google Scholar 

  61. Reunaud, C., Fall, Y., Feuersten, M., Doucet, H., and Santelli, M., Tetrahedron, 2009, vol. 65, p. 7440.

    Article  CAS  Google Scholar 

  62. Kulciţki, V., Bourdelais, A., Schuster, T., and Baden, D., Tetrahedron Lett., 2010, vol. 51, p. 4079.

    Article  CAS  Google Scholar 

  63. Khalilova, Yu.A., Spirikhin, L.V., Salikhov, Sh.M., and Valeev, F.A., Russ. J. Org. Chem., 2014, vol. 50, no. 1, p. 117.

    Article  CAS  Google Scholar 

  64. Molander, G.A. and Cooper, D.J., J. Org. Chem., 2007, vol. 72, p. 3558.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  65. Stallforth, P., Matthies, S., Adibekain, A., Gilligham, D.G., Hilvert, D., and Seeberger, P.H., Chem. Commun, 2012, vol. 48, p. 11987.

    Article  CAS  Google Scholar 

  66. Xu, S., Toyama, T., Nakamura, J., and Arimoto, H., Tetrahedron Lett., 2010, vol. 51, p. 4534.

    Article  CAS  Google Scholar 

  67. Xu, S., Arimoto, H., and Uemura, D., Angew. Chem., 2007, vol. 119, p. 5848.

    Article  Google Scholar 

  68. Xu, S., Unabara, D., Uemura, D., and Arimoto, H., Chem. Asian J., 2014, vol. 9, p. 367.

    Article  CAS  PubMed  Google Scholar 

  69. White, J.D., Grether, U.M., and Lee, C.-S., Org. Synth, 2005, vol. 82, p. 108.

    Article  CAS  Google Scholar 

  70. Garifullina, L.R., Salimova, E.V., Kasradze, V.G., Spirikhin, L.V., and Kukovinets, O.S., Chem. Nat. Compd., 2012, vol. 48, no. 5, p. 791.

    Article  CAS  Google Scholar 

  71. Tyagi, V. and Gupta, A.K., Synth. Commun., 2012, vol. 42, p. 843.

    Article  CAS  Google Scholar 

  72. Savchenko, R.G., Urazaeva, Ya.R., Kostyleva, S.A., and Odinokov, V.N., Russ. J. Org. Chem., 2013, vol. 49, no. 4, p. 610.

    Article  CAS  Google Scholar 

  73. Ishmuratov, G.Yu., Bannova, A.V., Latypova, E.R., Tukhvatshin, V.S., Kukovinets, O.S., Muslukhov, R.R., and Tolstikov, G.A., Russ. J. Org. Chem., 2013, vol. 49, no. 1, p. 42.

    Article  CAS  Google Scholar 

  74. Savchenko, R.G., Urazaeva, Ya.R., Shafikov, R.V., and Odinokov, V.N., Russ. J. Org. Chem., 2009, vol. 45, no. 8, p. 1149.

    Article  CAS  Google Scholar 

  75. Kyasa, S.K., Fisher, T.J., and Dussault, P.H., Synthesis, 2011, no. 21, p. 3475.

    Google Scholar 

  76. Wu, C.-Y., Lin, H.-C., and Wu, H.-J., Tetrahedron, 2012, vol. 68, p. 2100.

    Article  CAS  Google Scholar 

  77. Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Botsman, L.P., Idrisova, Z.I., Muslukhov, R.R., Ishmuratova, N.M., and Tolstikov, G.A., Russ. J. Org. Chem., 2013, vol. 49, no. 10, p. 1409.

    Article  CAS  Google Scholar 

  78. Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Botsman, L.P., Muslukhov, R.R., and Tolstikov, G.A., Russ. J. Org. Chem., 2014, vol. 50, no. 8, p. 1075.

    Article  CAS  Google Scholar 

  79. Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Botsman, L.P., Muslukhov, R.R., Ishmuratova, N.M., and Tolstikov, G.A., Russ. J. Org. Chem., 2014, vol. 50, no. 7, p. 928.

    Article  CAS  Google Scholar 

  80. Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Botsman, L.P., Muslukhov, R.R., and Tolstikov, G.A., Russ. J. Org. Chem., 2013, vol. 49, no. 10, p. 1415.

    Article  CAS  Google Scholar 

  81. Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Botsman, L.P., Muslukhov, R.R., and Tolstikov, G.A., Butlerov Commun., 2014, vol. 38, no. 6, p. 129.

    Google Scholar 

  82. Ishmuratov, G.Yu., Shayakhmetova, A.Kh., Yakovleva, M.P., Legostaeva, Yu.V., Shitikova, O.V., Galkin, E.G., and Tolstikov, G.A., Russ. J. Org. Chem., 2007, vol. 43, no. 8, p. 1114.

    Article  CAS  Google Scholar 

  83. Ishmuratov, G.Yu., Legostaeva, Yu.V., Botsman, L.P., Yakovleva, M.P., Shakhanova, O.O., Muslukhov, R.R., and Tolstikov, G.A., Chem. Nat. Compd., 2009, vol. 45, no. 3, p. 318.

    Article  CAS  Google Scholar 

  84. Ishmuratov, G.Yu., Legostaeva, Yu.V., Botsman, L.P., Muslukhov, R.R., Yakovleva, M.P., and Talipov, R.F., Vestn. Bashk. Univ., 2009, no. 1, p. 27.

    Google Scholar 

  85. Legostaeva, Yu.V., Garifullina, L.R., Nazarov, I.S., and Ishmuratov, G.Yu., Russ. J. Org. Chem., 2018, vol. 54, no. 1, p. 51.

    Article  CAS  Google Scholar 

  86. Legostaeva, Yu.V., Garifullina, L.R., Nazarov, I.S., Kravchenko, A.A., Kravchenko, L.V., and Ishmuratov, G.Yu., Russ. J. Org. Chem., 2016, vol. 52, no. 11, p. 1708.

    Article  CAS  Google Scholar 

  87. Legostaeva, Yu.V., Garifullina, L.R., Nazarov, I.S., Kravchenko, A.A., Ishmuratova, N.M., and Ishmuratov, G.Yu., Chem. Nat. Compd., 2017, vol. 53, no. 5, p. 891.

    Article  CAS  Google Scholar 

  88. Legostaeva, Yu.V., Garifullina, L.R., Nazarov, I.S., Nurieva, E.R., Kolotova, M.A., and Ishmuratov, G.Yu., Butlerov Commun., 2017, vol. 52, no. 11, p. 18.

    Google Scholar 

  89. Ishmuratov, G.Yu., Legostaeva, Yu.V., Garifullina, L.R., Botsman, L.P., Nasibullina, G.V., and Gazetdinov, R.R., Vestn. Bashk. Univ., 2014, vol. 19, no. 1, p. 29.

    Google Scholar 

  90. Raskil’dina, G.Z., Legostaeva, Yu.V., Garifullina, L.R., Sultanova, R.M., Ishmuratov, G.Yu., and Zlotskii, S.S., Lett. Org. Chem., 2016, vol. 13, no. 9, p. 652.

    Article  CAS  Google Scholar 

  91. Zabicky, J., The Chemistry of Peroxides, Rappoport, Z., Ed., Chichester: Wiley, 2006, part 1, p. 597.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yu. V. Myasoedova.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Myasoedova, Y.V., Nazarov, I.S. & Ishmuratov, G.Y. Transformations of Peroxide Products of Alkene Ozonolysis. Russ J Org Chem 55, 47–73 (2019). https://doi.org/10.1134/S107042801901007X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801901007X

Keywords

Navigation