Rearrangement of 1-Azidoadamantane to 3-Aryl-4-azahomoadamantane in the Presence of Aluminum Chloride and Aromatic Substrates

Article abstract of DOI:10.1021/jo00318a011

Reaction of 1-azidoadamantane (1) with aromatic substrates in the presence of aluminum chloride at 80 deg C for 1.25 h gave the corresponding 3-aryl-4-azahomoadamantane (2) in >90 percent yield.The reaction of 1 to 2 represents the first report of intermolecular aminoalkylation of aromatics in the benzene series, presumably from an imine intermediate.At 18 deg C, only 3-hydroxy-4-azahomoadamantane is obtained.Addition of water to the reaction system at 80 deg C yielded 1-phenyladamantane (4) as the major product.Mechanistic features are treated.