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- W2949204827 abstract "The oxidation of lineal, cyclic, and bicyclic aliphatic p-chlorobenzoic and p-chorobenzenesulfonic acid esters 2 with methyl(trifluoromethyl)dioxirane (TFDO) (1) occurs at positions in the hydrocarbon chain distant from the directing group with a significant degree of selectivity to give the corresponding keto or hydroxy esters. Compounds 2 are relatively deactivated with respect to this oxidation due to the electron-withdrawing nature of the ester moiety. Methylene Cα−H and Cβ−H bonds remain unchanged in all cases, but tertiary Cβ−H bonds undergo oxidation with TFDO (1). Stereoelectronic factors are used to explain the faster reaction rate in competition experiments for the oxidation of endo-norbornyl ester 2h than for its exo-isomer 2g." @default.
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- W2949204827 date "1996-01-01" @default.
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- W2949204827 title "Oxyfunctionalization of Aliphatic Esters by Methyl(trifluoromethyl)dioxirane" @default.
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- W2949204827 doi "https://doi.org/10.1021/jo9604189" @default.
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