75470-71-2Relevant academic research and scientific papers
Rearrangement of 1-Azidoadamantane to 3-Aryl-4-azahomoadamantane in the Presence of Aluminium Chloride and Aromatic Substrates
Margosian, Daniel,Sparks, David,Kovacic, Peter
, p. 275 - 276 (1980)
Reaction of 1-azidoadamantane with aromatic substrates in the presence of aluminium chloride gave the corresponding 3-aryl-4-azahomoadamantane, presumably via an imine intermediate.
Rearrangement of 1-Azidoadamantane to 3-Aryl-4-azahomoadamantane in the Presence of Aluminum Chloride and Aromatic Substrates
Margosian, Daniel,Kovacic, Peter
, p. 877 - 880 (2007/10/02)
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.
