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The regioselective [2 + 2] photocycloaddition reaction of 2-(3,4-dimethoxystyryl)quinoxaline in solution

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Abstract

Herein, the [2 + 2] photocycloaddition between two molecules of (E)-2-(3,4-dimethoxystyryl)-quinoxaline (1) in an acetonitrile solution to form only one cyclobutane isomer out of eleven possible isomers is described. The observed photocycloaddition reaction is reversible; thus, the studied photocycloaddition reaction can be considered as a photoreversible photochromic process. The removal of two methoxy groups from the (E)-2-(3,4-dimethoxystyryl)quinoxaline (1) structure produces compound 2, which participates only in the photoisomerization reaction. The change of the quinoxaline residue in 1 to quinoline results in the formation of compound 3, which demonstrates the regioselective oxidization electrocyclic transformation through the formation of a novel C–N bond.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova str. 28, 119991, Moscow, Russia

    Olga A. Fedorova, Alina E. Saifutiarova, Elena N. Gulakova, Tseimur M. Aliyeu, Nikolai E. Shepel & Yuri V. Fedorov

  2. D. Mendeleev University of Chemical Technology of Russia, Miusskaya sqr. 9, 125047, Moscow, Russia

    Olga A. Fedorova, Alina E. Saifutiarova & Elena O. Guskova

Authors
  1. Olga A. Fedorova
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  2. Alina E. Saifutiarova
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  3. Elena N. Gulakova
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  4. Elena O. Guskova
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  5. Tseimur M. Aliyeu
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  6. Nikolai E. Shepel
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  7. Yuri V. Fedorov
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Correspondence to Olga A. Fedorova.

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Electronic supplementary information (ESI) available. See DOI: 10.1039/c9pp00028c

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Fedorova, O.A., Saifutiarova, A.E., Gulakova, E.N. et al. The regioselective [2 + 2] photocycloaddition reaction of 2-(3,4-dimethoxystyryl)quinoxaline in solution. Photochem Photobiol Sci 18, 2208–2215 (2019). https://doi.org/10.1039/c9pp00028c

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  • DOI: https://doi.org/10.1039/c9pp00028c

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