Issue 9, 2019

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
15 1月 2019
Accepted
10 3月 2019
First published
13 3月 2019

Photochem. Photobiol. Sci., 2019,18, 2208-2215

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

O. A. Fedorova, A. E. Saifutiarova, E. N. Gulakova, E. O. Guskova, T. M. Aliyeu, N. E. Shepel and Y. V. Fedorov, Photochem. Photobiol. Sci., 2019, 18, 2208 DOI: 10.1039/C9PP00028C

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