Abstract
Reaction of 1,3-dehydroadamantane with ethyl esters of α-halocarboxylic acids occurs either at Cα–H bond, or at Cα–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.
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Original Russian Text © V.M. Mokhov, G.М. Butov, S.V. Dyakonov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 8, pp. 1166–1171.
For communication IV, see [1].
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Mokhov, V.M., Butov, G.М. & Dyakonov, S.V. 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. Russ J Org Chem 53, 1180–1185 (2017). https://doi.org/10.1134/S1070428017080048
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DOI: https://doi.org/10.1134/S1070428017080048