Collect. Czech. Chem. Commun. 1980, 45, 906-909

Nucleophilic substitution reaction of methyl 2-bromoethyl-3-(2-furyl)propenoate with amines

Vladimír Žvak, Jaroslav Kováč and Miroslav Kríž

Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava


Nucleophilic replacement of bromine in methyl 2-bromomethyl-3-(2-furyl)propenoate by amines (piperidine, morpholine, N-methylaniline, diethylamine and tert-butylamine) was studied. In all cases only products of direct substitution of bromine were obtained; this shows that a 2-furyl group in γ-position of an allylic system plays a decisive role in the change of mechanism, characteristic for keto allylic mobile systems.