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

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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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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Key words

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