Catalytic vapour-phase reactions of 2-hydroxymethylpyrrolidine and 2-aminomethyltetrahydrofuran over palladium–alumina

Abstract

Reactions of 2-hydroxymethylpyrrolidine and 2-aminomethyltetrahydrofuran over a palladium–alumina catalyst have been compared at 300 °C. During the ammonolysis of 2-hydroxymethyltetrahydrofuran, ammonia does not react with the substrate molecule before ring expansion has occurred. A surface transition intermediate is suggested in which adjacent catalytic sites are held jointly responsible for the ammonolysis and ring expansion of 2-hydroxymethyltetrahydrofuran to tetrahydropyridine.