Download PDF
Synthesis 1990; 1990(8): 646-648
DOI: 10.1055/s-1990-26967
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.

      >