The Triazene Moiety as a Protecting Group for Aromatic Amines

Article abstract of DOI:10.1021/jo00060a028

Reaction of (2-), (3-), and (4-bromophenyl)-3,3-(1,4-butanediyl)triazenes (derived from the corresponding 2-, 3-, and 4-bromoanilines) with sec- or tert-butyllithiums gave the corresponding (triazenylaryl)lithiums; these intermediates reacted with a variety of electrophiles to give substituted aryl triazenes.These products could be converted to substituted anilines by reduction or to novel substituted aromatics by a modified Sandmeyer reaction.