Electrochemistry of Anilines. 6. Reactions of Electrogenerated Biphenylylnitrenium Ions

Article abstract of DOI:10.1021/jo00015a019

3,5-Di-tert-butyl-substituted biphenyl-4-ylnitrenium ions are generated by anodic oxidation of the corresponding biphenylylamines in acetonitrile in the presence of a base.The reactions of these species with several nucleophiles are studied.The principal reaction sites are identified as the positions ortho and para to the =NH moiety.No reactions at the iminium nitrogen and in the second ring of the biphenyl system are observed.Products are characterized by spectroscopic techniques.Some common spectroscopic features of the iminoquinolide reaction products are discussed.