The Reactions of 3-Phenyl-1-propylamine-1-^(14)C and 3-(p-Methoxyphenyl)-1-propylamine-1-^(14)C with Nitrous Acid

3-Phenyl-l-propylamine-l-^(14)C reacts with nitrous acid in aqueous solution to give hydrocinnamyl alcohol, benzylmethyl-carbinol and allylbenzene. Under similar conditions, 3-(p-methoxyphenyl)-l-propylamine-l-^(14)C gives p-methoxyhydro-cinnamyl alcohol, p-methoxybenzylmethylcarbinol and p-,ethoxyallylbenzene. A negligible amount of isotope-position rearrangement attends the formation of the above products. The course of the reactions of 3-aryl-1-propylamines with nitrous acid discussed