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Photochemical transformations of chalcone-podands into cyclobutane-containing benzocrown ethers

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Abstract

A method for the synthesis of cyclobutane-containing benzocrown ethers by the template photocycloaddition of the corresponding chalcone-podands in solutions was developed. It was shown by X-ray diffraction analysis, 1H and 13C NMR, and UV spectroscopy that the intramolecular [2π+2π] photocycloaddition (PCA) is stereoselective with the predominant formation of structures of the β- and γ-truxinic type. The PCA rate was shown to depend on the size of the oxyethylene spacer and stereoorientation of the chalcone fragments in the podands. The selectivity of the PCA process can be controlled by a change in the concentration of the template (alkaline metal ions) and variation of the wavelength range of irradiation.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Chemistry, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620041, Ekaterinburg, Russian Federation

    I. G. Ovchinnikova, O. V. Fedorova, E. G. Matochkina, M. I. Kodess, P. A. Slepukhin & G. L. Rusinov

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  1. I. G. Ovchinnikova
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  2. O. V. Fedorova
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  3. E. G. Matochkina
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  4. M. I. Kodess
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  5. P. A. Slepukhin
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  6. G. L. Rusinov
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Correspondence to I. G. Ovchinnikova.

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Dedicated to Academician O. N. Chupakhin on the occasion of his 75th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1150–1160, June, 2009.

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Ovchinnikova, I.G., Fedorova, O.V., Matochkina, E.G. et al. Photochemical transformations of chalcone-podands into cyclobutane-containing benzocrown ethers. Russ Chem Bull 58, 1180–1191 (2009). https://doi.org/10.1007/s11172-009-0154-8

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  • DOI: https://doi.org/10.1007/s11172-009-0154-8

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