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Synlett 1990; 1990(12): 739-740
DOI: 10.1055/s-1990-21232
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Stereoselective Isomerisation of 2-Aryl-2-hydroxyadamantanes: A Convenient Method for (Z)-2-Aryl-5-hydroxyadamantanes

Vladimir V. Kovalev* , Andrey K. Rozov, Elvira A. Shokova<
  • *Department of Chemistry, Moscow State University, Lenin's Hills, Moscow, 119899, USSR
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Publication Date:
08 March 2002 (online)

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The isomerisation of a number of 2-aryl-2-hydroxyadamantanes 1a-h in trifluoroacetic acid is proposed as a good method for preparing the (Z) and (E) stereoisomers of 2-aryl-5-hydroxyadamantanes, 2a-h and 3a-h. Predominant formation of (Z)-isomers 2a -j is observed in all cases. The influence on the stereoselectivity and rate of the nature of the substituents on the aromatic ring, temperature, and time of the reaction is described.