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Behavior of 1-hydroxy-2,2,5,5-tetramethyl-3-imidazoline-3-oxide and the corresponding nitroxyl radicals in superacid media

  • Physical Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

The protonation of 1-R-2,2,5,5-tetramethyl-3-imidazoline-3-oxides (R=OH, O) in superacid media was investigated with1H and13C NMR. The hydroxylamino dication forming on protonation can undergo imidazoline ring opening to form an isomeric mixture of diprotonated N-(2-hydroxyimino-1,1-dimethylethyl),α,α-dimethylnitrones.

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Literature cited

  1. I. A. Grigor'ev, G. I. Shchukin, and L. B. Volodarskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2277 (1986).

    Google Scholar 

  2. I. A. Grigor'ev, V. I. Mamatyuk, G. I. Shchukin, V. V. Martin, and L. B. Volodarskii, Khim. Geterotsikl. Soedin., No. 8, 1065 (1986).

    Google Scholar 

  3. G. I. Shchukin and I. A. Grigor'ev, Imidazoline Nitroxyl Radicals [in Russian], Nauka, Novosibirsk (1988), p. 171.

    Google Scholar 

  4. P. Schiess and H. Stalder, Tetrahedron Lett.,21, 1413, 1416 (1980).

    Google Scholar 

  5. M. Casey, C. J. Moody, and C. W. Rees, J. Chem. Soc. Chem. Commun., 1082 (1983).

  6. V. A. Koptyug, Arenone Ions: Structure and Reactivity [in Russian], Nauka, Novosibirsk (1983).

    Google Scholar 

  7. L. B. Volodarskii and G. A. Kutikova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 937 (1971).

    Google Scholar 

  8. G. A. Olah and T. E. Kiovsky, J. Am. Chem. Soc.,90, 4666, 6461 (1968).

    Google Scholar 

  9. G. A. Olah, A. M. White, and D. H. Brien, Chem. Rev.,70, 561 (1970).

    Google Scholar 

  10. G. A. Olah and P. Kreienbühl, J. Am. Chem. Soc.,89, 4756 (1967).

    Google Scholar 

  11. L. B. Volodarskii, V. A. Reznikov, and V. S. Kobrin, Zh. Org. Khim.,15, 415 (1979).

    Google Scholar 

  12. A. A. Bothner-By, in: Advances in Magnetic Resonance, J. B. Waugh (ed.), Vol. 1, Academic Press, New York (1965), p. 195.

    Google Scholar 

  13. Yu. Yu. Samitov and S. V. Yalymova, Zh. Org. Khim.,8, 441 (1972).

    Google Scholar 

  14. Yu. G. Putsykin and L. B. Volodarskii, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 9(4), 86 (1969).

    Google Scholar 

  15. R. É. Valter, Ring-Chain Isomerism in Organic Chemistry [in Russian], Zinatne, Riga (1978).

    Google Scholar 

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Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, USSR

    S. V. Morozov, L. B. Volodarskii & V. G. Shubin

Authors
  1. S. V. Morozov
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  2. L. B. Volodarskii
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  3. V. G. Shubin
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2755–2761, December, 1991.

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Morozov, S.V., Volodarskii, L.B. & Shubin, V.G. Behavior of 1-hydroxy-2,2,5,5-tetramethyl-3-imidazoline-3-oxide and the corresponding nitroxyl radicals in superacid media. Russ Chem Bull 40, 2399–2404 (1991). https://doi.org/10.1007/BF00959709

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  • DOI: https://doi.org/10.1007/BF00959709

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