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Chemistry of Heterocyclic Compounds

, Volume 10, Issue 3, pp 270–275 | Cite as

Isomerism of 5-arylfurfural oximes (according to PMR spectroscopic data)

  • N. P. Kostyuchenko
  • A. F. Oleinik
  • T. I. Vozyakova
  • K. Yu. Novitskii
  • Yu. N. Sheinker
Article

Abstract

The stereochemistry of 5-arylfurfurals and their O-acetyl derivatives was studied by PMR spectroscopy. The configurations of each of the isomers were determined for the oximes of p-bromo- and p-chlorophenylfurfurals, which were isolated as two geometrical isomers, and also for their O-acetyl derivatives. The anti and syn configurations were established for the oximes of phenylfurfural and p-nitrophenylfurfural, respectively, which were obtained as single isomers. Conclusions regarding the preferred conformation of the side chain relative to the plane of the furan ring in all of the investigated isomers were drawn on the basis of an analysis of the of the long-range spin-spin coupling constants (\({\text{J}}_{{\text{H}}_{\text{0}} {\text{H}}_{\text{4}} } \)).

Keywords

Spectroscopy Organic Chemistry Furan Oxime Spectroscopic Data 
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 1975

Authors and Affiliations

  • N. P. Kostyuchenko
    • 1
  • A. F. Oleinik
    • 1
  • T. I. Vozyakova
    • 1
  • K. Yu. Novitskii
    • 1
  • Yu. N. Sheinker
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemistry InstituteMoscow

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