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

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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.

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Authors and Affiliations

  1. Photochemistry Center, Russian Academy of Sciences, 7A ul. Novatorov, 119421, Moscow, Russian Federation

    S. P. Gromov, A. I. Vedernikov, N. A. Lobova & M. V. Alfimov

  2. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russian Federation

    L. G. Kuz’mina

  3. A. V. Bogatsky Physicochemical Institute, National Academy of Sciences of Ukraine, 86 Lustdorfskaya doroga, 65080, Odessa, Ukraine

    S. S. Basok

  4. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    Yu. A. Strelenko

Authors
  1. S. P. Gromov
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  2. A. I. Vedernikov
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  3. L. G. Kuz’mina
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  4. N. A. Lobova
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  5. S. S. Basok
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  6. Yu. A. Strelenko
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  7. M. V. Alfimov
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Correspondence to S. P. Gromov.

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Dedicated to Academician A. I. Konovalov on his 75th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 108–114, January, 2009.

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Gromov, S.P., Vedernikov, A.I., Kuz’mina, L.G. et al. Stereoselective [2+2] photocycloaddition in bispseudosandwich complexes of bis(18-crown-6) stilbene with alkanediammonium ions. Russ Chem Bull 58, 108–114 (2009). https://doi.org/10.1007/s11172-009-0016-4

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  • DOI: https://doi.org/10.1007/s11172-009-0016-4

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