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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

Place Of Publication


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

Place Of Publication