Abstract
Adducts of [2 + 2]-cycloaddition to the 3–4 bond were isolated in the photochemical cycloaddition of vinyl butyl ether and acrylonitrile to 4-methyl-7-diethylaminocoumarin. The stereochemical structures of the compounds obtained as isomers of the ″head-to-tail″ type with an endo or exo orientation of the substituents were established by means of PMR spectroscopy. As a result of an evaluation of the effect of sensitizers and one-electron oxidizing and reducing agents it was found that the investigated reactions proceed through the singlet excited states of 7-aminocoumarins. It is assumed that the regiospecificity of the [2 + 2]-cycloaddition is determined by the C(3) reaction center of the coumarin fragment.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1169–1175, September, 1988.
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Kirpichenok, M.A., Mel'nikova, L.M., Denisov, L.K. et al. Photochemical reactions of 7-aminocoumarins 1. [2 + 2]-cycloadducts with vinyl butyl ether and acrylonitrile. Chem Heterocycl Compd 24, 959–965 (1988). https://doi.org/10.1007/BF00474037
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DOI: https://doi.org/10.1007/BF00474037