Pathways of ion–molecular interactions of nucleogenic phenyl cations with the nucleophilic centers of picolines

BACKGROUND: The nuclear-chemical method brought unique opportunity for synthesis of unknown and hardly available organic compounds. Presence of tritium labeling allows one-step preparation of radioactive markers for the investigation of chemical and biological processes. METHODS: The ion–molecular reactions of nucleogenic phenyl cations with 4-picoline have been carried out. The phenyl cations were generated by spontaneous tritium β-decay within the tritium-labeled benzene. Both additions to the nitrogen and substitutions about the aromatic ring were able to be studied simultaneously. RESULTS: Unusual substitutions on both the α- and β-positions of the ring system have been revealed. CONCLUSION: By unknown direct phenylation of nitrogen atom tritium-labeled N-phenylpicolinium derivatives, perspective biological markers have been synthesized.