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Russian Chemical Bulletin

, Volume 44, Issue 11, pp 2131–2136 | Cite as

Crown-ether styryl dyes

15. Synthesis and two pathways of regio- and stereospecific cation-dependent [2+2]-autophotocycloaddition of chromogenic 15-crown-5-ether betaines of quinoline series
  • S. P. Gromov
  • O. A. Fedorova
  • E. N. Ushakov
  • A. V. Buevich
  • M. V. Alfimov
Organic Chemistry

Abstract

Styryl dyes (4a,b) containing a 15-crown-5 fragment and isomeric 2- and 4-quinolinium residues with anN-sulfopropyl substituent undergo [2+2]-autophotocycloaddition to give cyclobutane derivatives (9a,b) in acetonitrile only in the presence of Mg(ClO4)2 or Ca(ClO4)2. The stereospecificity of both pathways of photocycloaddition and its efficiency are explained by the preorganization of the supramolecular dimers derived from thetrans-isomers of the dyes when they are bound into complexes with Mg and Ca cations.

Key words

crown ether styryl dyes complex-formation [2+2]-photocycloaddition cyclobutane derivatives 1H NMR spectra 

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Copyright information

© Plenum Publishing Corporation 1996

Authors and Affiliations

  • S. P. Gromov
    • 1
  • O. A. Fedorova
    • 1
  • E. N. Ushakov
    • 2
  • A. V. Buevich
    • 3
  • M. V. Alfimov
    • 1
  1. 1.N. N. Semenov Institute of Chemical PhysicsRussian Academy of SciencesMoscowRussian Federation
  2. 2.Institute of Chemical Physics in ChernogolovkaRussian Academy of SciencesChernogolovka, Moscow RegionRussian Federation
  3. 3.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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