Journal of Organic Chemistry p. 1613 - 1620 (1984)
Update date:2022-08-05
Topics: Oxidation Experimental Migrations
Goldstein, Stephen L.
McNelis, Edward
The oxidation of mesidine in methanolic media by ferricyanide, dichromate, and persulfate afforded an anil 4 containing a shifted methoxymethyl group in addition to the principal anil 3 formed by oxidative dealkylation.Possible intermediates 6, 7, and 8 were prepared and oxidized to the product anils.Oxidations of related anilines 9, 10, and 13 did not parallel those of mesidine but afforded analogues of 3.There is significant spectral evidence for anils with alkyl shifts but little for anils analogous to 4.
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