Rearrangements in the Reactions of 2-(4-Substituted)-phenylethylamines-1-C^(14) with Nitrous Acid

Treatment of a series of C^(14)-labeled 2-(4-substituted)-phenylethylamines (X-CH_2C^(14)H_2NH_2) with nitrous acid in water and acetic acid has been found to yield more or less of the isotope-position rearrangement products (X-C^(14)H_2CH_2Y; Y = -OH or -0Ac) depending on the solvent and the nature of X. With X = -OCH_8, -H and -NO_2, the most rearrangement (45%) was observed in acetic acid with X = -OCH_8, and the least (~5%) rearrangement when X = -NO_2 in water or acetic acid.