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Chemistry of Heterocyclic Compounds

, Volume 19, Issue 8, pp 824–831 | Cite as

Ring-chain tautomerism and thermo- and photochromism of 3-(1-hydroxy-4-methyl-2-naphthyl)propenal imines

  • I. M. Andreeva
  • O. M. Babeshko
  • E. M. Bondarenko
  • N. V. Volbushko
  • M. I. Knyazhanskii
  • E. A. Medyantseva
  • A. V. Metelitsa
  • V. I. Minkin
Article
  • 35 Downloads

Abstract

A series of previously undescribed 3-(1-hydroxy-4-methyl-2-naphthyl)propenal imines was synthesized. In the crystalline state all of the imines, except the N-(p-nitrophenyl)imine, have an open o-quinoid structure, whereas in solutions in nonpolar solvents they exist in the cyclic 2H-chromene form. In polar solvents the imines display ring-chain tautomeric equilibrium of the 2H-chromene and o-quinoid forms, the relative percentages of which are determined by the character of the substituent in the amino component of the molecule and by the polarity of the solvent. The N-(p-nitrophenyl)imine has-the 2H-chromene structure in the solid phase and in solvents.

Keywords

Organic Chemistry Polar Solvent Propenal Crystalline State Relative Percentage 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • I. M. Andreeva
    • 1
  • O. M. Babeshko
    • 1
  • E. M. Bondarenko
    • 1
  • N. V. Volbushko
    • 1
  • M. I. Knyazhanskii
    • 1
  • E. A. Medyantseva
    • 1
  • A. V. Metelitsa
    • 1
  • V. I. Minkin
    • 1
  1. 1.Rostov State UniversityRostov-on-Don

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