Abstract
It is shown that the reactivities of cyclic formals in the case of bromination with dioxane dibromide increase in the order 1,3-dioxepane > 1,3-dioxalane ≫ 1,3-dioxane, which is explained not only by steric factors but also by the ease of cleavage of the C4-O3 bond of the dioxacyclane ring. The bromination of cyclic acetals takes place through prior enolization of the cyclic acetal with subsequent electrophilic addition of bromine to the double bond.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 176–179, February, 1981.
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Kotlyar, S.A., Kamalov, G.L., Savranskaya, R.L. et al. Kinetics and mechanism of bromination of cyclic acetals with 1,4-dioxane dibromide. Chem Heterocycl Compd 17, 120–123 (1981). https://doi.org/10.1007/BF00507239
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DOI: https://doi.org/10.1007/BF00507239