Russian Journal of Physical Chemistry A

, Volume 93, Issue 1, pp 23–27 | Cite as

Effect of Solvents on Acid-Catalyzed Claisen Amino Rearrangement in N-(1-Methyl-2-butenyl)aniline

  • I. B. Abdrakhmanov
  • V. M. Sharafutdinov
  • A. G. Mustafin
  • Yu. S. ZiminEmail author
  • R. R. Daminev


The effect solvents have on the processes of rearrangement and elimination in N-(1-methyl-2-butenyl)aniline (I) in the presence of HCl is studied. It is shown that the dependence of the rearrangement and elimination rate constants of (I) · HCl on the nature of solvents are described perfectly by the Koppel–Palm equation, which considers both nonspecific and specific solvation. The inhibitory effect of solvent nucleophilicity is explained by the complexation between (I) · HCl and solvent molecules. Analysis of the (I) · HCl conversion products obtained in a mixed solvent (m-toluidine + nitrobenzene) demonstrates the intermolecular transfer of the allyl moiety, confirming the formation of allyl cations in the Claisen amino rearrangement.


N-(1-methyl-2-butenyl)aniline Claisen rearrangement acidic catalysis effect of solvents 



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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • I. B. Abdrakhmanov
    • 1
  • V. M. Sharafutdinov
    • 2
  • A. G. Mustafin
    • 3
  • Yu. S. Zimin
    • 3
    Email author
  • R. R. Daminev
    • 2
  1. 1.Ufa Institute of Chemistry, Russian Academy of SciencesUfaRussia
  2. 2.Ufa State University of Petroleum TechnologyUfaRussia
  3. 3.Bashkir State UniversityUfaRussia

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