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Reactions of α-pentafluorophenylpyrylium salts with hydroxylamine

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Abstract

The reactions of α-pentafluorophenylpyrylium salts with hydroxylamine in ethanol afford isoxazoline derivatives and/or pyridine N-oxides depending on the steric characteristics of the substituent in the second α position. The structure of 2-hydroxy-2-pentafluorophenyl-4-phenyl-2,3,5,6,7,8-hexahydroquinoline 1-oxide, which was synthesized by the reaction of 2-pentafluorophenyl-4-phenyl-5,6,7,8-tetrahydrobenzopyrylium perchlorate with NH2OH, was established by X-ray diffraction.

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References

  1. A. T. Balaban, A. Dinculescu, G. N. Dorofeenko, G. W. Fischer, A. V. Koblik, V. V. Mezheritskii, W. Schroth, Pyrylium Salts: Syntheses, Reactions, and Physical Properties. in Adv. Heterocycl. Chem., Ed. A. R. Katrizky, Suppl. 2. Academic Press, New York, 1982, 434 p.

    Google Scholar 

  2. V. M. Vlasov, Izv. SO Akad. Nauk SSSR, Ser. Khim., 1971, 96 [Bull. Sib. Branch Russ. Acad. Sci., Div. Chem. Sci., 1971 (Engl. Transl.)].

  3. N. A. Orlova, T. N. Gerasimova, M. A. Kudinova, A. I. Tolmachev, Zh. Org. Khim., 1990, 26, 1313 [J. Org. Chem. USSR, 1990, 26 (Engl. Transl.)].

    CAS  Google Scholar 

  4. W. R. Dolbier, Jr., J. Fluor. Chem., 2005, 126, 157.

    Article  CAS  Google Scholar 

  5. S. P. Sachchar, A. K. Singh, J. Indian Chem. Soc., 1985, 62, 142.

    CAS  Google Scholar 

  6. I. Yu. Kargapolova, N. A. Orlova, T. N. Gerasimova, Khim. Geterotsikl. Soedin., 1991, 1100 [Chem. Heterocycl. Compd., 1991, 27 (Engl. Transl.)].

    Google Scholar 

  7. A. T. Balaban, Tetrahedron, 1968, 24, 5059.

    Article  CAS  Google Scholar 

  8. C. Uncuţa, M. T. Căproiu, V. Câmpeanu, A. Petride, M. G. Dănilă, M. Plăveţi, A. T. Balaban, Tetrahedron, 1998, 54, 9747.

    Article  Google Scholar 

  9. C. Uncuţa, A. Tudose, M. T. Căproiu, M. Plăveţi, R. Kakou-Yao, Tetrahedron, 1999, 55, 15011.

    Article  Google Scholar 

  10. T. N. Gerasimova, E. P. Fokin, Usp. Khim., 1980, 49, 1057 [Russ. Chem. Rev., 1980, 49 (Engl. Transl.)].

    CAS  Google Scholar 

  11. R. S. Rowland, R. Taylor, J. Phys. Chem., 1996, 100, 7384.

    Article  CAS  Google Scholar 

  12. H. Suezawa, T. Yoshida, M. Hirota, H. Takahashi, Y. Umezawa, K. Honda, S. Tsuboyama, M. Nishio, J. Chem. Soc., Perkin Trans. 2, 2001, 2053.

  13. Cambridge Structural Database, University of Cambridge, Cambridge, UK, Version 5.27.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrentreva, 630090, Novosibirsk, Russian Federation

    I. Yu. Kargapolova, K. S. Shmuilovich, N. A. Orlova, M. M. Shakirov, T. V. Rybalova & V. V. Shelkovnikov

Authors
  1. I. Yu. Kargapolova
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  2. K. S. Shmuilovich
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  3. N. A. Orlova
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  4. M. M. Shakirov
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  5. T. V. Rybalova
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  6. V. V. Shelkovnikov
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Corresponding author

Correspondence to N. A. Orlova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 402–407, February, 2008.

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Kargapolova, I.Y., Shmuilovich, K.S., Orlova, N.A. et al. Reactions of α-pentafluorophenylpyrylium salts with hydroxylamine. Russ Chem Bull 57, 412–417 (2008). https://doi.org/10.1007/s11172-008-0064-1

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  • DOI: https://doi.org/10.1007/s11172-008-0064-1

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