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Chemistry of Heterocyclic Compounds

, Volume 25, Issue 5, pp 489–493 | Cite as

Benzenoid-quinoid tautomerism of azomethines and their structural analogs. 42. Synthesis, structures, and spectral-luminescence properties of 3-hydroxy-2-acetylbenzo[b]thiophene imines

  • E. N. Shepelenko
  • V. A. Bren'
  • A. D. Dubonosov
  • A. É. Lyubarskaya
  • V. I. Minkin
Article

Abstract

N-Aryl- and N-alkylimines of 3-hydroxy-2-acetylbenzo[b]-thiophene, the most stable isomeric form of which, according to the UV, IR, and 1H NMR spectra data, is the E-keto enamine structure, were synthesized. Irradiation of the aminovinyl ketones in the region of the long-wave absorption band causes thermally and photochemically reversible E⇄Z isomerization. 2-Aminoethylidene-3-(2H)-benzo[b]thiophenones have low-intensity fluorescence with a normal Stokesian shift, which is absent in solutions of their lithium and sodium salts.

Keywords

Lithium Absorption Band Ketone Thiophene Structural Analog 
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 1989

Authors and Affiliations

  • E. N. Shepelenko
    • 1
  • V. A. Bren'
    • 1
  • A. D. Dubonosov
    • 1
  • A. É. Lyubarskaya
    • 1
  • V. I. Minkin
    • 1
  1. 1.Scientific-Research Institute of Physical and Organic ChemistryM. A. Suslov Rostov State UniversityRostov-on-Don

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