Springer Online Journal Archives 1860-2000
Chemistry and Pharmacology
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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