Abstract
Anodic oxidation of various types of 2-methoxy-2,3,3,3-tetrafluoropropylamines, ArRNCH 2 Y [Y=CF(OMe)CF 3 ] was carried out in KOH/MeOH. Methoxylation α to the Y group and/or cleavage of a carbon–nitrogen bond took place depending on the kind of R groups. The regioselectivity of such methoxylation and C–N cleavage can be explained mainly in terms of the α -CH kinetic acidities of the cation radicals formed by one-electron oxidation of the amines. Furthermore, reasonable diastereoselectivity was obtained in the anodic methoxylation when the R group is alkyl. On the other hand, when the R group is aryl, the diastereoselectivity was extremely low.
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