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Addition of aliphatic and aromatic amines to catechol in aqueous solution under oxidizing conditions

Journal Article


Abstract


  • The oxidation of catechol in the presence of two aliphatic and aromatic amines has been investigated. In aqueous solutions of pH 7•0 and 11•7, the substitution pattern of the adduct was dependent on the type of amine used. Aromatic amines produced 4, 5-disubstituted o-quinones, whereas aliphatic amines gave either 2, 4, 5-trisubstituted or 2, 4-disubstituted o-quinone adducts. A rationale based upon the stability of vinylogous amides is presented to account for the observed substitution pattern. © 1989 ASEG.

Publication Date


  • 1989

Citation


  • Manthey, M. K., Pyne, S. G., & Truscott, R. J. W. (1989). Addition of aliphatic and aromatic amines to catechol in aqueous solution under oxidizing conditions. Australian Journal of Chemistry, 42(3), 365-373. doi:10.1071/CH9890365

Scopus Eid


  • 2-s2.0-84970583496

Web Of Science Accession Number


Start Page


  • 365

End Page


  • 373

Volume


  • 42

Issue


  • 3

Abstract


  • The oxidation of catechol in the presence of two aliphatic and aromatic amines has been investigated. In aqueous solutions of pH 7•0 and 11•7, the substitution pattern of the adduct was dependent on the type of amine used. Aromatic amines produced 4, 5-disubstituted o-quinones, whereas aliphatic amines gave either 2, 4, 5-trisubstituted or 2, 4-disubstituted o-quinone adducts. A rationale based upon the stability of vinylogous amides is presented to account for the observed substitution pattern. © 1989 ASEG.

Publication Date


  • 1989

Citation


  • Manthey, M. K., Pyne, S. G., & Truscott, R. J. W. (1989). Addition of aliphatic and aromatic amines to catechol in aqueous solution under oxidizing conditions. Australian Journal of Chemistry, 42(3), 365-373. doi:10.1071/CH9890365

Scopus Eid


  • 2-s2.0-84970583496

Web Of Science Accession Number


Start Page


  • 365

End Page


  • 373

Volume


  • 42

Issue


  • 3