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Reactions of hydroxyl-containing compounds with tert-butyl hydroperoxide in the presence of chromium tetra-tert-butoxide

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Abstract

Primary and secondary aliphatic, alkylaromatic, cyclic, and organoelement alcohols are efficiently oxidized by tert-butyl hydroperoxide in the presence of both equimolar and catalytic quantities of chromium tetra-tert-butoxide (С6Н6, 20°С). α-Diols containing tertiary hydroxyl groups interact with this system via oxidative splitting of the carbon scaffold. The oxidation includes the stages of formation and decomposition of chromium-containing peroxy compounds. Further transformations of the carbonyl compounds depend on the structure of radicals in the molecules.

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References

  1. Dodonov, V.?., Stepovik, L.P., Sofronova, S.M., and Mukhina, T.V., Zh. Obshch. Khim., 1988, vol. 58, no. 7, p. 1578.

    CAS  Google Scholar 

  2. Stepovik, L.P., Gulenova, M.V., and Martynova, I.M., Russ. J. Gen. Chem., 2005, vol. 75, no. 4, p. 507. DOI: 10.1007/s11176-005-0262-6.

    Article  CAS  Google Scholar 

  3. Stepovik, L.P., Gulenova, M.V., Tishkina, A.N., and Cherkasov, V.K., Russ. J. Gen. Chem., 2007, vol. 77, no. 7, p. 1254. DOI: 10.1134/S1070363207070183.

    Article  CAS  Google Scholar 

  4. Stepovik, L.P., Potkina, A.Yu., and Poddelskii, A.I., Russ. J. Gen. Chem., 2013, vol. 83, no. 11, p. 2005. DOI: 10.1134/S1070363213110066.

    Article  CAS  Google Scholar 

  5. Dodonov, V.B., Stepovik, L.P., and Sofronova, S.M., Zh. Obshch. Khim., 1981, vol. 51, no. 12, p. 2730.

    CAS  Google Scholar 

  6. Muzart, J., Chem. Rev., 1992, vol. 92, no. 1, p. 113. DOI: 10.1021/cr00009a005.

    Article  CAS  Google Scholar 

  7. Muzart, J., Tetrahedron Lett., 1987, vol. 28, no. 19, p. 2133. DOI: 10.1016/S0040-4039(00)96062-3.

    Article  CAS  Google Scholar 

  8. Riahi, A. Henin, Fand., Muzart, J., Tetrahedron Lett., 1999, vol. 40, no. 12, p. 2303. DOI: 10.1016/S0040-4039(99)00168-9.

    Article  CAS  Google Scholar 

  9. Alyea, E.C., Basi, J.S., Bradley, D.C., and Chisholm, M.H., J. Chem. Soc. (A), 1971, p. 772. DOI: 10.1039/J19710000772.

    Google Scholar 

  10. Gulenova, M.V., Stepovik, L.P., and Cherkasov, V.K., Russ. J. Gen. Chem., 2006, vol. 76, no. 6, p. 980. DOI: 10.1134/S1070363206060235.

    Article  CAS  Google Scholar 

  11. Tsuji, Y., Ohta, T., Ydo, T., and Minbu, H., J. Organometal. Chem., 1984, vol. 270, no. 2, p. 333. DOI: 10.1016/0022-328X(84)80381-2.

    Article  CAS  Google Scholar 

  12. Stepovik, L.P., Gulenova, M.V., Shavyrin, A.S., and Fukin, G.K., Russ. J. Gen. Chem., 2006, vol. 76, no. 8, p. 1275. DOI: 10.1134/S1070363206080202.

    Article  CAS  Google Scholar 

  13. Stepovik, L.P., Potkina, A.Yu., and Poddelskii, A.I., Russ. J. Gen. Chem., 2012, vol. 82, no. 9, p. 1805. DOI: 10.1134/S1070363213110066.

    Google Scholar 

  14. Stepovik, L.P., Malysheva, Yu.B., and Fukin, G.K., Russ. J. Gen. Chem., 2015, vol. 85, no. 6, p. 1401. DOI: 10.1134/S1070363215060080.

    Article  CAS  Google Scholar 

  15. Glushakova, V.N., Skorodumova, N.A., Nevodchikov, V.I., Abakumova, L.G., Makarenko, N.P., Cherkasov, V.K., and Druzhkov, N.O., Russ. Chem. Bull., 1999, vol. 48, no. 5, p. 934. DOI: 10.1007/BF02494640.

    Article  CAS  Google Scholar 

  16. Matsumoto, M. and Kuroda, K., J. Am. Chem. Soc., 1982, vol. 104, no. 5, p. 1433. DOI: 10.1021/ja00369a052.

    Article  CAS  Google Scholar 

  17. Funabiki, T., Mizoguchi, A., Sugimoto, T., Tada, S., Tsuji, M., Sakamoto, H., and Yohida, S., J. Am. Chem. Soc., 1986, vol. 108, no. 11, p. 2921. DOI: 10.1021/ja00271a022.

    Article  CAS  Google Scholar 

  18. Sawaki, Y. and Foote, C.S., J. Am. Chem. Soc., 1983, vol. 105, no. 15, p. 5035. DOI: 10.1021/ja00353a030.

    Article  CAS  Google Scholar 

  19. Sheldrick, G.M., SHELXTL v. 6.14, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA, 2003.

    Google Scholar 

  20. Sheldrick, G.M., TWINABS v.2012/1, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA, 2012.

    Google Scholar 

  21. CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171.NET) (compiled Apr 1 2005, 17:53:34).

  22. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171.NET) (compiled Apr 1 2005, 17:53:34).

  23. SCALE3 ABSPACK–An Oxford Diffraction Program (1.0.4, gui:1.0.3) (C), Oxford Diffraction, Ltd., 2005.

  24. Sheldrick, G.M., SHELXS-97: Program for Crystal Structure Solution, University of Göttingen, Germany, 1997.

    Google Scholar 

  25. Sheldrick, G.M., SHELXL-97: Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.

    Google Scholar 

  26. Spek, A.L., PLATON: A Multipurpose Crystallographic Tool, Utrecht: Utrecht University, 1999.

    Google Scholar 

  27. Palmer, W.G., Experimental Inorganic Chemistry, Cambridge: Cambridge University Press, 1954, p. 385.

    Google Scholar 

  28. Krauss, H.-L. and Munster, G., Z. Anorg. Allg. Chem., 1967, vol. 352, nos. 1–2, p. 24. DOI: 10.1002/zaac.19673520105.

    Article  CAS  Google Scholar 

  29. Speier, J., Daubert, B., and McGregor, R., J. Am. Chem. Soc., 1948, vol. 70, no. 3, p. 1117. DOI: 10.1021/ja01183a074.

    Article  CAS  Google Scholar 

  30. Dictionary of Organic Compounds, Moscow: Inostrannaya Literatura, 1949, vol. 3, p. 386; vol. 1, p. 259.

  31. Garcia-Delgado, N., Riera, A., and Verdaguer, X., Org. Lett., 2007, vol. 9, no. 4, p. 635. DOI: 10.1021/ol0629420.

    Article  CAS  Google Scholar 

  32. Weigand-Hilgetag, Experimental Methods in Organic Chemistry, Moscow: Khimiya, 1968, p. 715.

    Google Scholar 

  33. Agronomov, E.E. and Shabarov, Yu.S., Laboratornye raboty v organicheskom praktikume (Laboratory Works in Organic Workshop), Moscow: Khimiya, 1974, p. 128.

    Google Scholar 

  34. Ecke, G.G. and Kolka, A.J., US Patent 3075832, 1963.

    Google Scholar 

  35. Groysman, S., Villagram, D., and Nocera, D.G., Inorg. Chem., 2010, vol. 49, no. 23, p. 10759. DOI: 10.1021/ic101968s.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Lobachevskii Nizhny Novgorod State University, pr. Gagarina 23, Nizhny Novgorod, 603950, Russia

    L. P. Stepovik, E. A. Zaburdaeva & G. K. Fukin

  2. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, Nizhny Novgorod, Russia

    G. K. Fukin

  3. Department Chemie, Ludwig-Maximilians-Universität, München, Germany

    K. Karaghiosoff

Authors
  1. L. P. Stepovik
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  2. E. A. Zaburdaeva
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  3. G. K. Fukin
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  4. K. Karaghiosoff
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Correspondence to L. P. Stepovik.

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Original Russian Text © L.P. Stepovik, Е.А. Zaburdaeva, G.K. Fukin, K. Karaghiosoff, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 11, pp. 1805–1817.

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Stepovik, L.P., Zaburdaeva, E.A., Fukin, G.K. et al. Reactions of hydroxyl-containing compounds with tert-butyl hydroperoxide in the presence of chromium tetra-tert-butoxide. Russ J Gen Chem 85, 2547–2559 (2015). https://doi.org/10.1134/S1070363215110080

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  • DOI: https://doi.org/10.1134/S1070363215110080

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