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Synthesis 1990; 1990(8): 646-648
DOI: 10.1055/s-1990-26967
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Preparation of 1,3-Functionalized Adamantanes by the Lewis Acid Catalyzed Electrophilic Cyclization of 7-Methylenebicyclo[3.3.1]nonan-3-one in the Presence of π- and N-Nucleophiles

George A. Olah* , Ramesh Krishnamurti, G. K. Surya Prakash
  • *Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA
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Publication Date:
17 September 2002 (online)

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Preparation of 1,3-difunctionalized adamantane derivatives from 7-methylenebicyclo[3.3.1] nonane-3-one (1) in the presence of nucleophiles under Lewis acid catalysis is described. Reaction of 1 with benzene using a variety of Lewis acid catalysts gave 1,3-diphenyladamantane (4) as the major product. Trimethylsilyl cyanide and azide efficiently reacted with 1 in the presence of zinc iodide as the catalyst to give good yields of the corresponding 3-trimethylsiloxyadamantyl isocyanide and azide, respectively. Trimethylsilyl isothiocyanate gave a 1:1 mixture of the thiocyanate and isothiocyanate derivatives. Silyl enol ethers, such as those of acetophenone and cyclopentanone, and allyltrimethylsilane also reacted with 1 to afford the corresponding 1,3-difunctionalized adamantanes.