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


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.


Nitrogen Aluminum Chloride Organic Chemistry Nitrogen Atom 
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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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