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Chemistry of Heterocyclic Compounds

, Volume 22, Issue 6, pp 663–666 | Cite as

Course of bromination of thiazole and 2-methylthiazole

  • Ya. L. Gol'dfarb
  • G. P. Gromova
  • L. I. Belen'kii
Article

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.

Keywords

Nitrogen Aluminum Chloride Organic Chemistry Nitrogen Atom 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • Ya. L. Gol'dfarb
    • 1
  • G. P. Gromova
    • 1
  • L. I. Belen'kii
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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