Phenol oxidation and biosynthesis. Part XXV. New syntheses of bis-(2-arylethyl)amines of biosynthetic importance

Abstract

Two efficient routes to bis-(2-arylethyl)amines have been developed by using regiospecific alkylation of dialkylnitrosamine anions and homologation of aromatic aldehydes with methoxyacetonitrile anion as the respective key steps. The hitherto uncharacterised 1,3-diaryl-2-azonia-allene ions have been prepared in isolable form. Attempted insertion of C₁ fragments into these systems as a third route to the title compounds failed.