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
- Autores: Mokhov V.M.1, Butov G.М.2, Dyakonov S.V.2
-
Afiliações:
- Volgograd State Technical University
- Volzhsky Polytechnical University (Branch) of VolgSTU
- Edição: Volume 53, Nº 8 (2017)
- Páginas: 1180-1185
- Seção: Article
- URL: https://journals.rcsi.science/1070-4280/article/view/216680
- DOI: https://doi.org/10.1134/S1070428017080048
- ID: 216680
Citar
Resumo
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.
Sobre autores
V. Mokhov
Volgograd State Technical University
Email: butov@volpi.ru
Rússia, Volgograd
G. Butov
Volzhsky Polytechnical University (Branch) of VolgSTU
Autor responsável pela correspondência
Email: butov@volpi.ru
Rússia, ul. Engel’sa 42а, Volzhskii, Volgograd Region, 40412
S. Dyakonov
Volzhsky Polytechnical University (Branch) of VolgSTU
Email: butov@volpi.ru
Rússia, ul. Engel’sa 42а, Volzhskii, Volgograd Region, 40412
Arquivos suplementares
