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Abstract

This kinetic analysis compares homogeneous and heterogeneous catalysts for the cyclization of 6-aminohex-1-yne. The reaction was studied as a model for the direct addition of amine N[BOND]H bonds to CC multiple bonds (hydroamination). Kinetic modeling showed that the metal-catalyzed hydroamination reaction is followed by a proton-catalyzed isomerization of the primary reaction product, 2-methylene-piperidine, to the thermodynamically more stable 2-methyl-1,2-dehydropiperidine.