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Crown ether styryl dyes

24. Synthesis of multiphotochromic 15-crown-5 ethers with rigid spacers, their anion-”capped” complexes, and stereospecific [2+2] autophotocycloaddition

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

Novel styryl dyes (trans-2a,b) containing a 15-crown-5 ether moiety and anN-sulfobenzyl spacer were synthesized. The reactions oftrans-2a,b with Mg(ClO4)2 in MeCN afford dimeric complexes. During photolysis of the lattertrans-cis isomerization to give anion-“capped” complexes (cis-2a,b)·Mg2+ and stereospecific [2+2] autocycloaddition to yield cyclobutane derivative occur in parallel The ratio of the two transformation pathways of dyes2a,b depends on the spacer type. To interpret the experimental data, the molecular-mechanics and semiempirical quantum-chemical calculations were performed.

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Authors and Affiliations

  1. Center of Photochemistry, Russian Academy of Sciences, 7a ul. Novatorov, 117421, Moscow, Russian Federation

    S. P. Gromov, O. A. Fedorova, A. V. Lindeman & M. V. Alfimov

  2. Institute of Chemical Physics in Chernogolovka, Russian Academy of Sciences, 142432, Chernogolovka, Moscow Region, Russian Federation

    E. N. Ushakov & E. V. Malysheva

  3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    I. I. Baskin

  4. M. M. Shemyakin and Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 ul. Miklukho-Maklaya, 117871, Moscow, Russian Federation

    T. A. Balashova & A. S. Arsen'ev

Authors
  1. S. P. Gromov
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  2. O. A. Fedorova
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  3. E. N. Ushakov
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  4. I. I. Baskin
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  5. A. V. Lindeman
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  6. E. V. Malysheva
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  7. T. A. Balashova
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  8. A. S. Arsen'ev
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  9. M. V. Alfimov
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Additional information

For Part 23, see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 99–107, January, 1998.

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Gromov, S.P., Fedorova, O.A., Ushakov, E.N. et al. Crown ether styryl dyes. Russ Chem Bull 47, 97–106 (1998). https://doi.org/10.1007/BF02495515

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  • DOI: https://doi.org/10.1007/BF02495515

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