Chemistry of Heterocyclic Compounds p. 663 - 666 (1986)
Update date:2022-08-04
Topics: Yield Bromination Reaction Time Product Thiazole Reactant
Gol'dfarb, Ya. L.
Gromova, G. P.
Belen'kii, L. I.
Bromination of thiazole by bromine in the presence of aluminium 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 aluminium chloride; this is due to heterocycle deactivation by complexation with the Lewis acid at the nitrogen atom.
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(1931)
