Chemical transformations of tetracyclo[3.3.1.1.3,7.0.1,3]decane (1,3-dehydroadamantane): V. Reactions of 1,3-dehydroadamantane with esters of α-halogen-containing carboxylic acids

Abstract

Reaction of 1,3-dehydroadamantane with ethyl esters of α-halocarboxylic acids occurs either at C^α–H bond, or at C^α–Hlg bond. The regioselectivity of the reaction depends on the nature of the halogen. The ability of 1,3-dehydroadamantane to react at the C–Hlg grows in the series C–F < C–Cl < C–Br, which correlates with the energies of C–Hlg bonds. Difficultly available 1-R-3-halogen-substituted derivatives of adamantane were prepared under mild conditions in high yields.