Über die Stereochemie der Hydrogenolyse von N‐Benzyl‐Bindungen II. Die Deuteriolyse von chiralem N,N‐Dimethyl‐phenylglycin und die Konfiguration von (+)‐Phenyl‐essigsäure‐2‐d 1

The steric course of the hydrogenolytic cleavage of benzyl‐N‐bonds using Pd‐C catalyst was determined by deuteriolysis of R (−)‐N,N‐dimethyl‐phenylglycine I, which gave (+)‐phenylacetic acid containing 70% of the monodeutero compound. The configuration of (+)‐phenylacetic acid‐2‐d 1 was determined ( S ) and its optical purity estimated by Schmidt degradation to chiral S (+)‐benzylamine‐α‐d 1 . On the basis of these results, hydrogenolysis of I can be evaluated to proceed by 80% inversion and 20% retention of configuration. Methyl N,N‐dimethyl‐phenyl‐glycinate yielded racemized methyl phenylacetate‐2‐d 1 .