Issue 5, 1972

Benzoquinone imines. Part IX. Mechanism and kinetics of the reaction of p-benzoquinone di-imines with m-aminophenols

Abstract

The products of the coupling of p-benzoquinone di-imines with m-aminophenols indicate that reaction occurs in the position para to the hydroxy-group to give aminoindoanilines while, if this position is blocked, reaction occurs at the position para to the amino-group to give hydroxyindamines. The reaction of di-imine with 3-amino-4,6-dimethylphenol results in an equilibrium with a compound which is probably a pseudo-quinone imine. Kinetic studies show the reaction of di-imines with m-aminophenols to involve electrophilic attack of the conjugate acid of the di-imine on the phenolate ion and the neutral phenol, the former predominating at pH < 8. Kinetic studies also show that, with 4- and 6-methyl-3-aminophenol, some of the postulated pseudo-quinone imine is formed, but is ultimately converted into the normal indo-dye.

Aminoindoaniline reacts with p-phenylenediamine or other primary arylamines to give trinuclear indoanilines such as (VII) and (VIII). In concentrated solution, hydroxyindamines undergo intramolecular cyclization to give aminophenoxazineimines.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1972, 539-548

Benzoquinone imines. Part IX. Mechanism and kinetics of the reaction of p-benzoquinone di-imines with m-aminophenols

J. F. Corbett, J. Chem. Soc., Perkin Trans. 2, 1972, 539 DOI: 10.1039/P29720000539

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