Rearrangement in the Reaction of C^(14)-Labeled n-Propylamine (1-Aminopropane-1-C^(14)) with Nitrous Acid

Ethylamine-1-C^(14) on treatment with aqueous nitrous acid has been shown to yield, besides ethylene, a mixture of 98.5% of ethanol-l-C^(14) and 1.5% of ethanol-2-C^(14). It was concluded that if the ethyl cation is an important intermediate in the reaction of ethylamine with nitrous acid it reacts with water considerably more rapidly than it is converted to the ethyleneprotonium ion (I).