The Deamination of Deuterated-2-Hydroxy-2-Phenyl-3-Aminonorbornanes

2-endo-Hydroxy-2-phenyl-3-endo-aminonorbornane-5,6-exo-d₂ was synthesized and subjected to nitrous acid deamination in glacial acetic acid. From the cationic rearrangement reaction eight products were isolated by liquid elution chromatography and identified by nuclear magnetic resonance spectroscopy. 2-exo-Hydroxy-2-phenyl-3-endo-aminonorbornane was also synthesized and deaminated under similar conditions. The product yields from this compound as well as the product yields from the 2-endo-hydroxy amine were determined by vapor phase chromatography.

From an examination of the deuterium distribution in the products of the deuterated amine and from the yields of products from both amines it was possible to construct a reasonable reaction sequence for the deamination reaction. In addition, because of the deuterium distribution in the products, it was concluded that the intermediate ions in the reaction are principally classical in nature.