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- W2074421839 abstract "The oxidation of 2-substituted adamantanes (2) with TFDO (1) is reported. The data show a stereodifferentiation of the chemical environments induced by remote electron-withdrawing substituents which produces remarkable Z/E diastereoselectivity in the oxidation of the tertiary C(5)-H and C(7)-H bonds. The results show a bell-shaped correlation between the Z/E stereoselectivity and the substituent constant sigma(I), which is interpreted in terms of hyperconjugative stabilization of the diastereomeric transition states." @default.
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- W2074421839 date "2000-02-24" @default.
- W2074421839 modified "2023-10-09" @default.
- W2074421839 title "Hyperconjugative Control by Remote Substituents of Diastereoselectivity in the Oxygenation of Hydrocarbons" @default.
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- W2074421839 doi "https://doi.org/10.1021/ol000017m" @default.
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