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Course of bromination of thiazole and 2-methylthiazole

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Bromination of thiazole by bromine in the presence of aluminum chloride in neutral solvent or without solvent takes place at the 2-position. Such an orientation contradicts the traditional addition-cleavage mechanism, and agrees with the ylid mechanism of electrophilic substitution. 2-Methylthiazole brominates at the 5-position, and the reaction is impeded in the presence of aluminum chloride; this is due to heterocycle deactivation by complexation with the Lewis acid at the nitrogen atom.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, 117913, Moscow

    Ya. L. Gol'dfarb, G. P. Gromova & L. I. Belen'kii

Authors
  1. Ya. L. Gol'dfarb
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  2. G. P. Gromova
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  3. L. I. Belen'kii
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Deceased.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 837–840, June, 1986.

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Gol'dfarb, Y.L., Gromova, G.P. & Belen'kii, L.I. Course of bromination of thiazole and 2-methylthiazole. Chem Heterocycl Compd 22, 663–666 (1986). https://doi.org/10.1007/BF00575251

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  • DOI: https://doi.org/10.1007/BF00575251

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