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Solvent-free oxidation of aliphatic alcohols with ceric ammonium nitrate—lithium bromide system

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Abstract

Esters are formed during the solvent-free oxidation of primary aliphatic C5–C9 alcohols with Ce(NH4)2(NO3)6–LiBr, whereas secondary octan-2-ol gives a mixture of isomeric 1-and 3-bromooctan-2-ones.

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References

  1. V. Nair, L. Balagopal, R. Rajan, and J. Mathew, Acc. Chem. Res., 2004, 37, 21.

    Article  CAS  Google Scholar 

  2. V. Nair, S. B. Panicker, L. G. Nair, T. G. George, and A. Augstine, Synlett, 2003, 156.

  3. R. Varala, R. Enugala, S. Nuvula, and S. R. Adaqa, Synlett, 2006, 1009.

  4. R. H. Tale, Org. Lett., 2002, 4, 1641.

    Article  CAS  Google Scholar 

  5. A. Szummy and C. Wawrzenczyk, Synlett, 2006, 1523.

  6. W. Chen, X. Huang, H. Zhou, and L. Ren, Synthesis, 2006, 609.

  7. W.-B. Pan, F.-R. Chang, L.-M. Wei, M.-J. Wu, and Y.-C. Wu, Tetrahedron Lett., 2003, 44, 331.

    Article  CAS  Google Scholar 

  8. K. Pachamuthu and Y. D. Vankar, J. Chem. Soc., 2001, 66, 7511.

    CAS  Google Scholar 

  9. Z. Duan, X. Xuan, T. Li, C. Yang, and Y. Wu, Tetrahedron Lett., 2006, 47, 5433.

    Article  CAS  Google Scholar 

  10. V. S. Sridharan, C. Avendano, and J. C. Menendez, Synlett, 2007, 881.

  11. G. Maiti and Ch. Roy, Synth. Comm., 2002, 32, 2269.

    Article  CAS  Google Scholar 

  12. I. E. Marko, A. Ates, A. Gautier, B. Leory, J. M. Pluncher, Y. Quesnel, and J. Vanherk, Angew. Chem., Int. Ed., 1999, 38, 3207.

    Article  CAS  Google Scholar 

  13. W. S. Trahanovsky, M. G. Young, and P. M. Nave, Tetrahedron Lett., 1962, 2501.

  14. M. P. Doyle, L. S. Zuidema, and T. R. Bade, J. Chem. Soc., 1975, 40, 1454.

    CAS  Google Scholar 

  15. W. S. Trahanovsky, in Methods in Free-Radical Chemistry, Ed. E. S. Huyser, Marcel Dekker, New York, 1973, vol. 4, 133.

    Google Scholar 

  16. M. G. Vinogradov, I. P. Kovalev, and G. I. Nikishin, Usp. Khim., 1986, 55, 1979 [Russ. Chem. Rev., 1986, 55, 1130 (Engl. Transl.)].

    CAS  Google Scholar 

  17. N. I. Kapustina, L. L. Sokova, V. D. Makhaev, A. P. Borisov, and G. I. Nikishin, Izv. Akad. Nauk, Ser. Khim., 2000, 1870 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1842].

    Google Scholar 

  18. A. Schulz, G. Pagona, and A. Giannis, Synth. Commun., 2006, 36, 1147.

    Article  Google Scholar 

  19. N. I. Kapustina, A. V. Lisitsyn, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 98 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 38, 86 (Engl. Transl.)].

    Google Scholar 

  20. R. Bilterys and J. Gisseleire, Bull. Soc. Chim. Belg., 1935, 44, 574.

    Google Scholar 

  21. V. V. Zorin, R. R. Bikbulatov, L. N. Zorina, and D. L. Rakhmankulov, Zh. Org. Khim., 1997, 33, 511 [Russ. J. Org. Chem., 1997, 33, 453 (Engl. Transl.)].

    Google Scholar 

  22. S. I. Zav’yalov, G. I. Ezhova, I. V. Sitkareva, O. V. Dorofeeva, A. G. Zavozin, and E. E. Rumyantseva, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2392 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 38, 2204 (Engl. Transl.)].

    Google Scholar 

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Correspondence to N. I. Kapustina.

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Dedicated to Academician V. A. Tartakovsky in honor of his 75th anniversary.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1445—1450, August, 2007.

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Kapustina, N.I., Sokova, L.L., Gasanov, R.G. et al. Solvent-free oxidation of aliphatic alcohols with ceric ammonium nitrate—lithium bromide system. Russ Chem Bull 56, 1501–1506 (2007). https://doi.org/10.1007/s11172-007-0232-8

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  • DOI: https://doi.org/10.1007/s11172-007-0232-8

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