50348-20-4Relevant articles and documents
Oxidative Cross-Coupling of Some 2,6- and N,N-Disubstituted Aniline Derivatives with 4-Aminophenol Mediated by Cerium(IV) Ions in Aqueous Perchloric Acid
Domagala,Dziegiec
, p. 749 - 757 (2007/10/03)
The mechanism of the oxidation of mixtures of 2,6-dimethylaniline (1), N,N-dimethylaniline (2), 2,6-diethylaniline (3), N,N-diethylaniline (4), N-methylaniline (5), 2,6-difluoroaniline (6), and 2,3,5,6-tetrafluoroaniline (7) with 4-aminophenol (8) by cerium(IV) ions in aqueous perchloric acid has been investigated. The indoaniline salts [O=C6H4=N-C6H2(R1) 2NH(R2)2]+ClO- 4 (R1 = H, R2 = CH3, C2H5 or vice versa) are formed as intermediates in the cross-coupling reaction; they undergo oxidation to imino-4-benzoquinone (9) and its corresponding derivatives by cerium(IV) ions in high yields. The mechanism of this process is discussed.
Migrations in Oxidations of Mesidine
Goldstein, Stephen L.,McNelis, Edward
, p. 1613 - 1620 (2007/10/02)
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.