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Effects of substituents in acid-catalyzed Claisen amino rearrangement

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

A series of 4-R2-N-R1-N-(1-methyl-2-butenyl)- and 4-R2-N-R1-2-(1-methyl-2-butenyl)-anilines was synthesized. The rate constants of rearrangement and elimination of the hydrochlorides of the 4-R2-N-R1-N-(-1methyl-2-butenyl)anilines in nitrobenzene were measured at 110 and 130°C. The correlation equations which describe the effect of the nature of the substituents on the reactivity of the substrate in these reactions and the selectivity of their occurrence were established. A mechanism of the processes was proposed.

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Literature cited

  1. I. B. Abdrakhmanov, V. M. Sharafutdinov, N. G. Nigmatullin, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1273 (1983).

    Google Scholar 

  2. S. Jolidon and H. J. Hansen, Helv. Chim. Acta,60, 978 (1977).

    Google Scholar 

  3. S. Jolidon and H. J. Hansen, Chimia,30, 21 (1976).

    Google Scholar 

  4. C. Weygand and G. Hilgetag (eds.), Organisch-chemische Experimentierkunst, 3rd ed., Barth, Leipzig (1964).

    Google Scholar 

  5. I. B. Abdrakhmanov, V. M. Sharafutdinov, U. M. Dzhemilev, et al., Zh. Prikl. Khim., 2121 (1982).

  6. E. T. Denisov, Kinetics of Homogeneous Chemical Reactions, Vyssh. Shkola, Moscow (1978), p. 135.

    Google Scholar 

  7. Yu. A. Zhdanov and V. I. Minkin, Correlation Analysis in Organic Chemistry, Izd. Rost. Univ. (1966), pp. 106, 232.

  8. H. Becker, Einfuehrung in die Elektronentheorie organisch-chemischer Reaktionen, VEB Deutscher Verlag der Wissenschaften, Berlin (1961).

    Google Scholar 

  9. F. Keri and R. Sandberg, Advanced Course in Organic Chemistry [Russian translation], Khimiya, Moscow (1981), p. 355.

    Google Scholar 

  10. D. Bethell and V. Gold, Carbonium Ions, Academic Press, New York (1967).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Chemistry, Bashkir Scientific Center, Ural Branch, Academy of Sciences of the USSR, Ufa

    I. B. Abdrakhmanov, Z. N. Saraeva, N. G. Nigmatullin, V. D. Komissarov & G. A. Tolstikov

  2. Bashkir Institute of Agriculture, Ufa

    I. B. Abdrakhmanov, Z. N. Saraeva, N. G. Nigmatullin, V. D. Komissarov & G. A. Tolstikov

Authors
  1. I. B. Abdrakhmanov
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  2. Z. N. Saraeva
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  3. N. G. Nigmatullin
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  4. V. D. Komissarov
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  5. G. A. Tolstikov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2303–2308, October, 1989.

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Abdrakhmanov, I.B., Saraeva, Z.N., Nigmatullin, N.G. et al. Effects of substituents in acid-catalyzed Claisen amino rearrangement. Russ Chem Bull 38, 2117–2122 (1989). https://doi.org/10.1007/BF00962120

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  • DOI: https://doi.org/10.1007/BF00962120

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