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Iodo- and chlorodemercuration of 5,5′-mercuribisuracils

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The direct C mercuration in the 5 position of 1-acetyluracil by means of mercury (II) trifluoroacetate in anhydrous acetonitrile is described. The intermediately formed 1-acetyl-5-trifluoroacetoxymercuriuracil, without isolation, was subjected to symmetrization by the action of potassium iodide. The acetyl groups were then readily split out by the action of water. The resulting 5,5′-mercuribisuracil (50% yield) forms 5-iodo- or a 5-chlorouracil in 93% or 72% yields, respectively, under the influence of an aqueous KI3 solution or excess pure liquid S2Cl2.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 386–389, March, 1985.

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Wroczyński, P., Kujawa, A. & Skul'ski, L. Iodo- and chlorodemercuration of 5,5′-mercuribisuracils. Chem Heterocycl Compd 21, 322–325 (1985). https://doi.org/10.1007/BF00506675

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  • DOI: https://doi.org/10.1007/BF00506675

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