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Synthesis and structure of products of hydroxylamine acylation with 3-carboxy-2,2,5,5-tetramethylpyrrolinoxyl derivatives

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Abstract

The reaction of NH2OH with the derivatives of 2,2,5,5-tetramethylpyrrolin-1-oxyl-3-carboxylic acid in all events led to the formation of a mixture of the corresponding nitroxylhydroxamic acid with a stable O-acylhydroxylamine. The ratio between the products depends on the nature of the acylating agent and under the studied conditions varies from ∼5.5: 1 to 1: 3 indicating the comparable nucleophilicity in this reaction of N and O atoms in the hydroxylamine. The most active chloride of the mentioned acid alongside the indicated products afforded in a considerable yield N,O-diacylhydroxylamine and the triacylated hydroxylamine, 3-{[(2,2,5,5-tetramethyl-1-oxylopyrrolin-3-yl)carbonyloxyimino][(2,2,5,5-tetramethyl-1-oxylopyrrolin-3-yl)carbonyloxy]-methyl}-2,2,5,5-tetramethylpyrrolin-1-oxyl. The structure of both latter compounds was established by XRD analysis.

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References

  1. Sen’, V.D., Shilov, G.V., and Golubev, V.A., Zh. Org. Khim., 2008, vol. 44, p. 1193.

    Google Scholar 

  2. Marmion, C.J., Griffith, D., and Nolan, K.B. Eur. J. Inorg. Chem., 2004, p. 3003.

  3. Soule, B.P., Hyodo, F., Matsumoto, K., Simone, N.L., Cook, J.A., Krishna, M.C., and Mitchell, J.B., Free Rad. Biol. Med., 2007, vol. 42, p. 1632.

    Article  CAS  Google Scholar 

  4. Giacomelli, G., Porcheddu, A., and Salaris, M., Org. Lett., 2003, p. 2715.

  5. Barlaam, B., Hamon, A., and Maudet, M., Tetrahedron Lett., 1998, vol. 39, p. 7865.

    Article  CAS  Google Scholar 

  6. Pirrung, M.C. and Chau, J.H.-L., J. Org. Chem., 1995, vol. 60, p. 8084.

    Article  CAS  Google Scholar 

  7. Sen’, V.D. and Golubev, V.A., J. Phys. Org. Chem., 2009, vol. 22, p. 138.

    Article  Google Scholar 

  8. Litvin, E.F., Kozlova, L.M., Shapiro, A.B., Rozantsev, E.G., and Freidlin, L.Kh., Izv. Akad. Nauk SSSR, Ser. Khim., 1975, p. 1353.

  9. Bauer, L. and Exner, O., Angew Chem., Int. Ed., 1974, vol. 13, p. 376.

    Article  Google Scholar 

  10. Zhungietu, G.I. and Artemenko, A.I., Gidroksamovye kisloty i ikh proizvodnye (Hydroxamic Acids and Its Derivatives), Kishinev: Shtinitsa, 1986, p. 9.

    Google Scholar 

  11. Pilipenko, A.T. and Zul’figarov, O.S., Gidroksamovye kisloty (Hydroxamic Acids), Moscow: Nauka, 1989, p. 25.

    Google Scholar 

  12. Goettlicher, S. and Ochsenreiter, P., Chem. Ber., 1974, vol. 107, p. 398.

    Article  CAS  Google Scholar 

  13. Schraml, J., Mindl, J., Roithova, J., Blechta, V., Sykora, J., Soukupova, L., Karban, J., Bartlova, M., and Exner, O., Organometallics, 2004, vol. 23, p. 2157.

    Article  CAS  Google Scholar 

  14. Schraml, J., Sykora, J., Fiedler, P., Roithova, J., Mindl, J., Blechta, V., Cnsarova, I., and Exner, O., Org. Biomol. Chem., 2004, vol. 2, p. 2311.

    Article  CAS  Google Scholar 

  15. Grassi, G., Cordaro, M., Bruno, G., and Nicolo, F., Helv. Chim. Acta, 2002, vol. 85, p. 196.

    Article  CAS  Google Scholar 

  16. Buchachenko, A.L. and Vasserman, A.M., Stabil’nye radikaly (Stable Radicals), Moscow: Khimiya, 1973, 408 p.

    Google Scholar 

  17. Hudson, A. and Luckhurst, G., Chem. Rev., 1969, vol. 69, p. 191.

    Article  CAS  Google Scholar 

  18. Jencks, W.P., J. Am. Chem. Soc., 1958, vol. 80, p. 4581.

    Article  CAS  Google Scholar 

  19. Usova, E.M. and Voronin, E.M., Dokl. Akad. Nauk SSSR, 1957, vol. 113, p. 1306.

    CAS  Google Scholar 

  20. Exner, O., Coll. Czech. Chem. Commun., 1962, vol. 27, p. 2284.

    CAS  Google Scholar 

  21. Rozantsev, E.G. and Sholle, V.D., Organicheskaya khimiya svobodnykh radikalov (Organic Chemistry of Free Radicals), Moscow: Khimiya, 1979, p. 195.

    Google Scholar 

  22. Artemenko, A.I., Tikunova, I.V., Anufriev, E.K., Ehlicka, V., and Exner, O., Coll. Czech. Chem. Commun., 1981, vol. 46, p. 729.

    CAS  Google Scholar 

  23. Mazera, D.J., Gesser, J.C., and Pliego, J.R., ARKIVOC, 2007, vol. 15, p. 199.

    Google Scholar 

  24. Scott, A.W. and Wood, B.L., J. Org. Chem., 1942, vol. 7, p. 508.

    Article  CAS  Google Scholar 

  25. Rozantsev, E.G. and Krinitskaya, L.A., Tetrahedron, 1965, vol. 21, p. 491.

    Article  CAS  Google Scholar 

  26. Krinitskaya, L.A., Buchachenko, A.L., and Rozantsev, E.G., Zh. Org. Khim., 1966, vol. 2, p. 1301.

    CAS  Google Scholar 

  27. Hoffman, B.M., Schofield, P., and Pich, A., Proc. Nat. Acad. Sci. USA, 1969, vol. 62, p. 1195.

    Article  CAS  Google Scholar 

  28. Griffith, O.H., Keana, J.F., Noall, D.L., and Ivey, J.L., Biochem. Biophys. Acta, 1967, vol. 148, p. 583.

    CAS  Google Scholar 

  29. Brauer, G., Ed., Handbuch der Praparativen Anorganischen Chemie, Stuttgart: Ferdinand Enke Verlag, 1978.

    Google Scholar 

  30. Sheldrick, G.M., SHELXTL, v. 6.14. Structure Determination Software Suite, Bruker AXS, Madison, WI, USA.

  31. Sen’, V.D., Golubev, V.A., and Efremova, N.N., Izv. Akad. Nauk SSSR, Ser. Khim., 1982, p. 61.

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow oblast, 142432, Russia

    V. D. Sen’, G. V. Shilov & V. A. Golubev

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  1. V. D. Sen’
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  2. G. V. Shilov
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  3. V. A. Golubev
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Correspondence to V. D. Sen’.

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Original Russian Text © V.D. Sen’, G.V. Shilov, V.A. Golubev, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 8, pp. 1199–1208.

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Sen’, V.D., Shilov, G.V. & Golubev, V.A. Synthesis and structure of products of hydroxylamine acylation with 3-carboxy-2,2,5,5-tetramethylpyrrolinoxyl derivatives. Russ J Org Chem 45, 1189–1199 (2009). https://doi.org/10.1134/S1070428009080132

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