A mechanistic exploration of the liquid phase hydrogenation of the aromatic cyanohydrin mandelonitrile (C₆H₅CH(OH)CH₂CN) over a carbon supported Pd catalyst to produce the primary amine, phenethylamine (C₆H₅CH₂CH₂NH₂) is conducted. Prior examination showed the reaction to involve the production of the ketone intermediate 2-aminoacetophenone (C₆H₅C(O)CH₂NH₂), formed as a consequence of the presence of an acid catalysed tautomeric side reaction. The corresponding deuteration reaction, reported here and analysed by multinuclear NMR spectroscopy and mass spectrometry, is employed to further investigate accessible pathways. Examination of the resultant product distribution of the deuteration, and the location of deuterium incorporation establishes the role of a hydroxy-imine species as a key reaction intermediate. In addition, the acid catalysed tautomerism to the ketone is shown to be a reversible side reaction, but also a contributor to desired product formation. Moreover, an order for the three critical hydrogen consuming steps in phenethylamine formation is established. Hydrogenation of the nitrile functionality to afford the hydroxy-imine precedes hydrogenolysis of the hydroxyl group, with the final step being hydrogenation of the imine to form the target product, phenethylamine.

在碳负载的Pd催化剂上对芳香族氰醇扁桃腈（C ₆ H ₅ CH（OH）CH ₂ CN）进行液相加氢以生产伯胺苯乙胺（C ₆ H ₅ CH ₂ CH ₂ NH _2）的机理研究）进行。事先检查显示该反应涉及酮中间体2-氨基苯乙酮（C ₆ H ₅ C（O）CH ₂ NH ₂），是由于酸催化的互变异构副反应的存在而形成的。本文报道并通过多核NMR光谱和质谱分析的相应氘化反应用于进一步研究可及的途径。对氘化的最终产物分布以及氘结合位置的检查确定了羟基亚胺类物质作为关键反应中间体的作用。另外，显示出酮的酸催化的互变异构是可逆的副反应，但也是所需产物形成的原因。此外，建立了苯乙胺形成中三个关键氢消耗步骤的顺序。腈官能团的加氢反应生成羟基亚胺，然后羟基被氢解，