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N-alkylation of vinyloxyanilines with glycidyl ethers of phenols and a study of their basicity in acetonitrile

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

Conclusions

  1. 1.

    N-(2-Hydroxy-3-aryloxypropyl)vinyloxyanilines have been obtained for the first time by reaction of vinyloxyanilines with glycidyl esters of phenols.

  2. 2.

    A linear relationship has been established linking the size of the pK a with the Hammett constants of substituents in an aromatic series of anilines (ρ=3.26).

  3. 3.

    In acetonitrile the basicity of N-(2-hydroxy-3-aryloxypropyl)vinyloxyanilines was increased as a result of additional stabilization of the conjugate acids of these bases by an intramolecular hydrogen bond.

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Authors and Affiliations

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

    Z. V. Stepanova, Z. B. Efendiev, T. V. Kashik, G. V. Rassolova, O. B. Bannikova & G. G. Skvortsova

Authors
  1. Z. V. Stepanova
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  2. Z. B. Efendiev
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  3. T. V. Kashik
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  4. G. V. Rassolova
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  5. O. B. Bannikova
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  6. G. G. Skvortsova
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2321–2326, October, 1984.

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Stepanova, Z.V., Efendiev, Z.B., Kashik, T.V. et al. N-alkylation of vinyloxyanilines with glycidyl ethers of phenols and a study of their basicity in acetonitrile. Russ Chem Bull 33, 2120–2125 (1984). https://doi.org/10.1007/BF00954095

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  • DOI: https://doi.org/10.1007/BF00954095

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