Course of bromination of thiazole and 2-methylthiazole
Journal Article
·
· Chem. Heterocycl. Compd. (Engl. Transl.); (United States)
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.
- Research Organization:
- Academy of Sciences of the USSR, Moscow
- OSTI ID:
- 7043384
- Journal Information:
- Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 22:6; ISSN CHCCA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALUMINIUM CHLORIDES
ALUMINIUM COMPOUNDS
AZOLES
BROMINATION
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
COMPLEXOMETRY
HALIDES
HALOGEN COMPOUNDS
HALOGENATION
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
INORGANIC ACIDS
KINETICS
LEWIS ACIDS
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
REACTION KINETICS
THIAZOLES
YIELDS
400201* -- Chemical & Physicochemical Properties
ALUMINIUM CHLORIDES
ALUMINIUM COMPOUNDS
AZOLES
BROMINATION
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
COMPLEXOMETRY
HALIDES
HALOGEN COMPOUNDS
HALOGENATION
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
INORGANIC ACIDS
KINETICS
LEWIS ACIDS
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
REACTION KINETICS
THIAZOLES
YIELDS