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Russian Chemical Bulletin

, Volume 58, Issue 9, pp 1955–1961 | Cite as

Stereospecific [2+2] photocycloaddition in a pseudodimeric complex between N-ammoniopropylstyrylpyridine and 18-crown-6-containing styrylpyridine

  • A. I. Vedernikov
  • S. K. Sazonov
  • L. G. Kuz’mina
  • J. A. K. Howard
  • M. V. Alfimov
  • S. P. Gromov
Full Articles

Abstract

A quaternary 4-styrylpyridinium salt having the N-ammoniopropyl substituent forms a pseudodimeric head-to-tail complex with neutral 18-crown-6-containing 4-styrylpyridine in MeCN through H-bonding. This complex undergoes stereospecific [2+2] photocycloaddition due to preorganization of the ethylene bonds in the syn-arranged chromophoric fragments of the components. The structure of the rctt-isomer of the cyclobutane derivative obtained was established by NMR spectroscopy and X-ray diffraction analysis.

Key words

styryl dyes styrylheterocycles crown ethers ammonium ions complexation [2+2] photocycloaddition cyclobutanes X-ray diffraction study 

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Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • A. I. Vedernikov
    • 1
  • S. K. Sazonov
    • 1
  • L. G. Kuz’mina
    • 2
  • J. A. K. Howard
    • 3
  • M. V. Alfimov
    • 1
  • S. P. Gromov
    • 1
  1. 1.Photochemistry CenterRussian Academy of SciencesMoscowRussian Federation
  2. 2.N. S. Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussian Federation
  3. 3.Department of ChemistryUniversity of DurhamDurhamUK

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