Advertisement

Russian Chemical Bulletin

, Volume 58, Issue 6, pp 1211–1216 | Cite as

Stereospecific [2+2] autophotocycloaddition in the dimeric complex of 18-crown-6 ether styryl dye bearing N-(3-ammoniopropyl) substituent

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

Abstract

New 18-crown-6 ether styryl dye of the 4-pyridine series bearing N-(3-ammoniopropyl) substituent has been synthesized. In MeCN, the dye forms a stable dimeric complex of the syn-head-to-tail type due to the complexation of the ammonium group of one molecule with the crown ether fragment of another. In the dimeric complex, the ethylene bonds of the molecules are close in space and antiparallel, which promotes an efficient stereospecific [2+2] autophotocycloaddition to yield the only rctt-isomer of 1,2,3,4-tetrasubstituted cyclobutane. The cyclobutane derivative structure was confirmed by NMR spectroscopy and X-ray diffraction.

Key words

styryl dyes crown ethers ammonium ions complexation [2+2] photocycloaddition cyclobutanes 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    J.-M. Lehn, Supramolecular Chemistry. Concepts and Perspectives, VCH, Weinheim, 1995.Google Scholar
  2. 2.
    J. W. Steed, J. L. Atwood, Supramolecular Chemistry, J. Wiley and Sons, New York-Weinheim, 2000.Google Scholar
  3. 3.
    S. P. Gromov, Rossiiskie nanotekhnologii [Russian Nanotechnologies], 2006, 1, № 1–2, 29 (in Russian).Google Scholar
  4. 4.
    S. P. Gromov, E. N. Ushakov, A. I. Vedernikov, N. A. Lobova, M. V. Alfimov, Yu. A. Strelenko, J. K. Whitesell, M. A. Fox, Org. Lett., 1999, 1, 1697.CrossRefGoogle Scholar
  5. 5.
    S. P. Gromov, A. I. Vedernikov, E. N. Ushakov, N. A. Lobova, A. A. Botsmanova, L. G. Kuz’mina, A. V. Churakov, Yu. A. Strelenko, M. V. Alfimov, J. A. K. Howard, D. Johnels, U. G. Edlund, New J. Chem., 2005, 29, 881.CrossRefGoogle Scholar
  6. 6.
    E. N. Ushakov, V. A. Nadtochenko, S. P. Gromov, A. I. Vedernikov, N. A. Lobova, M. V. Alfimov, F. E. Gostev, A. N. Petrukhin, O. M. Sarkisov, Chem. Phys., 2004, 298, 251.CrossRefGoogle Scholar
  7. 7.
    S. P. Gromov, A. I. Vedernikov, N. A. Lobova, L. G. Kuz’mina, S. N. Dmitrieva, O. V. Tikhonova, M. V. Alfimov, Pat. RF 2278134; Byul. isobret. [Bull. Invent.], 2006, No. 17 (in Russian).Google Scholar
  8. 8.
    A. I. Vedernikov, S. K. Sazonov, P. S. Loginov, N. A. Lobova, M. V. Alfimov, S. P. Gromov, Mendeleev Commun., 2007, 17, 29.CrossRefGoogle Scholar
  9. 9.
    A. I. Vedernikov, S. P. Gromov, N. A. Lobova, L. G. Kuz’mina, Yu. A. Strelenko, J. A. K. Howard, M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim., 2005, 1896 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1954].Google Scholar
  10. 10.
    A. I. Vedernikov, E. N. Ushakov, N. A. Lobova, A. A. Kiselev, M. V. Alfimov, S. P. Gromov, Izv. Akad. Nauk, Ser. Khim., 2005, 656 [Russ. Chem. Bull., Int. Ed., 2005, 54, 666].Google Scholar
  11. 11.
    A. I. Vedernikov, L. G. Kuz’mina, S. K. Sazonov, N. A. Lobova, P. S. Loginov, A. V. Churakov, Yu. A. Strelenko, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, Izv. Akad. Nauk, Ser. Khim., 2007, 1797 [Russ. Chem. Bull., Int. Ed., 2007, 56, 1860].Google Scholar
  12. 12.
    L. G. Kuz’mina, A. I. Vedernikov, N. A. Lobova, A. V. Churakov, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, New J. Chem., 2007, 31, 980.CrossRefGoogle Scholar
  13. 13.
    C. Frassineti, S. Ghelli, P. Gans, A. Sabatini, M. S. Moruzzi, A. Vacca, Anal. Biochem., 1995, 231, 374.CrossRefGoogle Scholar
  14. 14.
    SAINT, Version 6.02A, Bruker AXS Inc., Madison, Wisconsin (USA), 2001.Google Scholar
  15. 15.
    SHELXTL-Plus, Version 5.10, Bruker AXS Inc., Madison, Wisconsin (USA), 1997.Google Scholar

Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • S. P. Gromov
    • 1
  • N. A. Lobova
    • 1
  • A. I. Vedernikov
    • 1
  • L. G. Kuz’mina
    • 2
  • J. A. K. Howard
    • 3
  • 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.Department of ChemistryUniversity of DurhamDurhamUK

Personalised recommendations