NUCLEOPHILIC CLEAVAGE OF N-O BOND IN O-(2,4-DINITROPHENYL)CYCLOHEXANONE OXIME IN AQUEOUS-METHANOL

Article abstract of DOI:10.1016/S0040-4020(01)88682-8

The order of nucleophilic reactivity towards nitrogen in o-(2,4-dinitrophenyl)cyclohexanone oxime with various nucleophiles in aqueous-methanol has been found to be: N2H4 > OH^- > PhO^- > urea > thiourea > SO3^- > CH3COO^- > NO2^- > S2O3^2- > SCN^- > Cl^- > Br^-.A SN₂ type of reaction involving a polar transition state on the oxime N is indicated.Bronsted relationship is applicable (β=0.09).The substrate is reducible at the dropping mercury electrode.Kinetics of the reaction has been followed both spectrophotometrically and polarographically with excellent conformity.