Journal of Organic Chemistry p. 607 - 615 (1994)
Update date:2022-09-26
Topics:
Fuchigami, Toshio
Ichikawa,, Shinji
Anodic methoxylation of various types of N-(fluoroethyl)amines, ArRNCH2Rf (Rf = CF3, CHF2, CH2F, etc.) has been systematically studied and it was found that a methoxy group was exclusively or preferentially introduced into the position α to the fluoromethyl (Rf) group, depending on the Rf and R groups.The effect of the Rf group on the promotion of the anodic α-methoxylation decreased in the order CF3, CHF2, and CH2F.This remarkable promotion effect and unique regioselectivity can be explained mainly in terms of the α-CH kinetic acidities of the cation radicals formed by one-electron oxidation of the amines.The α-methoxylated products are highly useful precursors for the construction of carbon-carbon bonds α to the trifluoromethyl and difluoromethyl groups, which is difficult by other methods.
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