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Model studies for insect protein sclerotization: Oxidative loss of the side chain from 4-substituted catechols

Journal Article


Abstract


  • The oxidation of several 4-substituted catechols in aqueous solution, pH7 in the presence of aniline results in the formation of 4,5-dianilino-1,2-benzoquinone 2 and the anil of 2, (3). The C-4 substituent is efficiently cleaved and mechanisms are proposed to account for this phenomenon based on HPLC and GC studies and the formation of N-methylaniline when these reactions were performed in the presence of sodium cyanoborohydride. The evidence suggests that the initial step involves the addition of aniline to the catechol C-4 side chain. © 1990.

Publication Date


  • 1990

Citation


  • Pyne, S. G., Truscott, R. J. W., Karin, M. M., Morales, C., Walsh, B. C., & Wynn, B. L. (1990). Model studies for insect protein sclerotization: Oxidative loss of the side chain from 4-substituted catechols. Tetrahedron, 46(2), 661-670. doi:10.1016/S0040-4020(01)85447-8

Scopus Eid


  • 2-s2.0-0041641733

Web Of Science Accession Number


Start Page


  • 661

End Page


  • 670

Volume


  • 46

Issue


  • 2

Abstract


  • The oxidation of several 4-substituted catechols in aqueous solution, pH7 in the presence of aniline results in the formation of 4,5-dianilino-1,2-benzoquinone 2 and the anil of 2, (3). The C-4 substituent is efficiently cleaved and mechanisms are proposed to account for this phenomenon based on HPLC and GC studies and the formation of N-methylaniline when these reactions were performed in the presence of sodium cyanoborohydride. The evidence suggests that the initial step involves the addition of aniline to the catechol C-4 side chain. © 1990.

Publication Date


  • 1990

Citation


  • Pyne, S. G., Truscott, R. J. W., Karin, M. M., Morales, C., Walsh, B. C., & Wynn, B. L. (1990). Model studies for insect protein sclerotization: Oxidative loss of the side chain from 4-substituted catechols. Tetrahedron, 46(2), 661-670. doi:10.1016/S0040-4020(01)85447-8

Scopus Eid


  • 2-s2.0-0041641733

Web Of Science Accession Number


Start Page


  • 661

End Page


  • 670

Volume


  • 46

Issue


  • 2