The Journal of Organic Chemistry

Adamantanes and related compounds. 16. Rearrangement of 1-azidoadamantane to 3-aryl-4-azahomoadamantane in the presence of aluminum chloride and …

D Margosian, P Kovacic

Index: Margosian, Daniel; Kovacic, Peter Journal of Organic Chemistry, 1981 , vol. 46, # 5 p. 877 - 880

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Citation Number: 11

Abstract

Reaction of 1-azidoadamantane (1) with aromatic substrates in the presence of aluminum chloride at 80 OC for 1.25 h gave the corresponding 3-aryl-4-azahomoadamantane (2) in> 90% 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" C, only 3- hydroxy-4-azahomoadamantane is obtained. Addition of water to the reaction system at ...

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