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Russian Chemical Bulletin

, Volume 58, Issue 1, pp 108–114 | Cite as

Stereoselective [2+2] photocycloaddition in bispseudosandwich complexes of bis(18-crown-6) stilbene with alkanediammonium ions

  • S. P. Gromov
  • A. I. Vedernikov
  • L. G. Kuz’mina
  • N. A. Lobova
  • S. S. Basok
  • Yu. A. Strelenko
  • M. V. Alfimov
Full Articles

Abstract

Due to hydrogen bonding, bis(18-crown-6) stilbene forms 1 : 1, 1 : 2, and 2 : 2 complexes with H3N+(CH2) n NH3 + 2ClO4 salts (n = 2—10, 12). The length of the polymethylene chain in the diammonium ions affects the phototransformation direction of stilbene and the composition of the products. In the 2: 2 bispseudosandwich complexes with relatively short alkanediammonium ions (n = 2—4), the stereoselective reaction of [2+2] photocycloaddition proceeds to form mainly the rctt-isomer of the cyclobutane derivative. The structure of rctt-cyclobutane derivative as a complex with H3N+(CH2)4NH3 +2ClO4 - was confirmed by X-ray diffraction analysis.

Key words

stilbenes crown ethers alkanediammonium ions complexation [2+2] photocycloaddition cyclobutanes X-ray diffraction analysis 

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Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • S. P. Gromov
    • 1
  • A. I. Vedernikov
    • 1
  • L. G. Kuz’mina
    • 2
  • N. A. Lobova
    • 1
  • S. S. Basok
    • 3
  • Yu. A. Strelenko
    • 4
  • M. V. Alfimov
    • 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.A. V. Bogatsky Physicochemical InstituteNational Academy of Sciences of UkraineOdessaUkraine
  4. 4.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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