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Mechanism of disproportionation of 2,2,6,6-tetramethyl-1,4-dioxopiperidinium perchlorate in acidic aqueous medium

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Abstract

The cation of 2,2,6,6-tetramethyl-1,4-dioxopiperidinium perchlorate disproportionates in acidic aqueous medium to give piperidinoxyl and/or 1-hydroxypiperidine, nitrone, and acetone. A mechanism of this reaction was proposed and the rate constants for its particular steps were calculated.

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References

  1. V. A. Golubev, Y. N. Kozlov, A. N. Petrov, A. P. Purmal, Progr. React. Kinet., 1991, 16, 35.

    CAS  Google Scholar 

  2. A. E. J. de Nooy, A. S. Besemer, H. van Bekkum, Synthesis, 1996, 1153.

  3. N. Merbouh, J. M. Bobbitt, C. Brückner, Org. Prep. Proc. Int., 2004, 36, 1.

    Article  CAS  Google Scholar 

  4. G. Tojo, M. Fernandez, in Oxidation of Alcohols to Aldehydes and Ketones, Springer, New York, 2006, p. 241.

    Google Scholar 

  5. F. A. Carey, R. J. Sundberg, in Advanced Organic Chemistry, 5th ed., Springer, New York, 2007, Part B, p. 1074.

    Google Scholar 

  6. V. A. Golubev, E. G. Rozantsev, M. B. Neiman, Izv. Akad. Nauk SSSR. Ser. Khim., 1965, 1927 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1965, 14, 1898].

  7. J. R. Fish, S. G. Swarts, M. D. Sevilla, T. Malinsky, J. Phys. Chem., 1988, 92, 3745.

    Article  CAS  Google Scholar 

  8. G. Moad, E. Rizzardo, D. H. Solomon, Tetrahedron Lett., 1981, 22, 1165.

    Article  CAS  Google Scholar 

  9. T. Endo, T. Miyazava, S. Shiihashi, M. Okawara, J. Am. Chem. Soc., 1984, 106, 3877.

    Article  CAS  Google Scholar 

  10. D. T. Sawyer, J. L. Roberts, Acc. Chem. Res., 1988, 21, 469.

    Article  CAS  Google Scholar 

  11. V. D. Sen’, V. A. Golubev, I. V. Kulyk, E. G. Rozantsev, Izv. Akad. Nauk SSSR, Ser. Khim., 1976, 1745 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1976, 25, 1647].

    Google Scholar 

  12. V. D. Sen’, Izv. Akad. Nauk, Ser. Khim., 1993, 548 [Russ. Chem. Bull. (Engl. Transl.), 1993, 42, 507].

  13. S. Fukuzumi, T. Yorisue, J. Am. Chem. Soc., 1991, 113, 7764.

    Article  CAS  Google Scholar 

  14. M. Ballester, I. Pascual, J. Org. Chem., 1991, 56, 841.

    Article  CAS  Google Scholar 

  15. V. A. Golubev, V. D. Sen’, 4th Int. Conf. on Nitroxide Radicals (Novosibirsk, 2005, 20–24 September), Novosibirsk, 2005, p. 94.

  16. V. D. Sen’, V. A. Golubev, T. M. Kosheleva, Izv. Akad. Nauk SSSR. Ser. Khim., 1979, 2001 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1979, 28, 1847].

  17. V. A. Golubev, V. D. Sen’, E. G. Rozantsev, Izv. Akad. NaukSSSR. Ser. Khim., 1979, 2091 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1979, 28, 1927].

  18. V. A. Golubev, V. D. Sen’, I. V. Kulyk, A. L. Aleksandrov, Izv. Akad. Nauk SSSR. Ser. Khim. 1975, 2235 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1975, 24, 2119].

  19. V. D. Sen’, V. A. Golubev, J. Phys. Org. Chem. 2009, 22, 138.

    Article  Google Scholar 

  20. V. A. Golubev, V. N. Borislavskii, A. L. Aleksandrov, Izv. Akad. Nauk SSSR. Ser. Khim., 1977, 2025 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1977, 26, 1874].

  21. Z. M. Skorobogatova, V. A. Golubev, A. K. Sheinkman, Khim. Geterotsikl. Soedin., 1981, 78 [Chem. Heterocycl., Compd. (Engl. Transl.), 1981].

  22. V. A. Golubev, R. I. Zhdanov, V. M. Gida, E. G. Rozantsev, Izv. Akad. Nauk SSSR. Ser. Khim., 1971, 853 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1971, 20, 768].

    Google Scholar 

  23. D. S. C. Black, A. B. Boscacci, Aust. J. Chem., 1976, 29, 2511.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    V. A. Golubev & V. D. Sen’

Authors
  1. V. A. Golubev
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  2. V. D. Sen’
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Correspondence to V. A. Golubev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1767–1770, September, 2009.

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Golubev, V.A., Sen’, V.D. Mechanism of disproportionation of 2,2,6,6-tetramethyl-1,4-dioxopiperidinium perchlorate in acidic aqueous medium. Russ Chem Bull 58, 1824–1827 (2009). https://doi.org/10.1007/s11172-009-0248-3

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  • DOI: https://doi.org/10.1007/s11172-009-0248-3

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