MODEL STUDIES FOR INSECT PROTEIN SCLEROTIZATION: OXIDATIVE LOSS OF THE SIDE CHAIN FROM 4-SUBSTITUTED CATECHOLS

Article abstract of DOI:10.1016/S0040-4020(01)85447-8

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.