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Homolytic replacement of a hydrogen atom in 2-methylquinoline by A 1,3-dioxolanyl residue

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 1,3-dioxolane with sulfuric-acid-protonated 2-methylquinoline initiated by the ROOH + Fe2+ system [where R = H, (CH3)3C, or C6H5C(CH3)2] at 5–10 °C in water forms 4-(1,3-dioxacyclopent-2-yl)-2-methylquinoline and 4-(1,3-dioxacy-clopent-4-yl)-2-methylquinoline. The selectivity of the formation of the first reaction product increases on passing from hydrogen peroxide to cumyl and tert-butyl hydroperoxide and with an increase in the pH of the medium.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 25–28, January, 1984.

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Zorin, V.V., Zelechonok, Y.B., Zlotskii, S.S. et al. Homolytic replacement of a hydrogen atom in 2-methylquinoline by A 1,3-dioxolanyl residue. Chem Heterocycl Compd 20, 20–23 (1984). https://doi.org/10.1007/BF00505841

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  • DOI: https://doi.org/10.1007/BF00505841

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