57123-48-5Relevant academic research and scientific papers
Oxidative Coupling of N,N- and 2,6-Disubstituted Aniline Derivatives Mediated by Cerium(IV) Ions in Aqueous Perchloric Acid
Seliger, Piotr,Wodzinska, Magdalena,Dziegiec, Jozef
, p. 249 - 256 (1999)
N,N- and 2,6-disubstituted anilines were oxidized by cerium(IV) perchlorate in aqueous solutions of perchloric acid to the corresponding derivatives of 4,4′-diphenoquinonediimine and N-phenyl-p-phenylenediimine in high yields. The type of the products obtained was determined by the properties of the substituents, by steric hindrance, and by the concentration of protons in the reaction mixtures. On the basis of experimental data and quantum mechanical calculations, which were performed using the semi-empirical AM1 method, a reaction mechanism was suggested.
Chemical consequences of fluorine substitution. Part 4. Diels-Alder reactions of fluorinated p-benzoquinones with Dane's diene. Synthesis of fluorinated D-homosteroids
Essers, Michael,Haufe, Guenter
, p. 2719 - 2728 (2007/10/03)
Four fluorinated p-benzoquinones (2) have been reacted with Dane's diene (1) in Diels-Alder reactions and the formed fluorinated D-homosteroids were characterized. The number of products, their stereochemistry and stability depends on the fluorine substitution pattern of the corresponding fluorinated p-benzoquinones. If the p-benzoquinone (2) contains an unfluorinated double bond, this bond reacts faster with diene 1 yielding endo-products selectively. In contrast, [4+2]cycloadditions with 2,6-difluoro (2c) and 2,3,5,6-tetrafluorobenzoquinone (2d) gave the products with exo-orientation of the carbonyl part preferably.
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.
