The reactions of monomeric phenolic lignin model compounds with cyanamide activated hydrogen peroxide were studied. Analyses of the various reaction products indicate four main reactions occur; aromatic hydroxylation, demethoxyiation, radical coupling and oxidative ring opening. The predominate products from apocynol and acetoguaiacohe were dicarboxylic acid compounds, maleic/fumaric, oxalic, and succinic acid derivatives, consistent with degradation by Superoxide. In the degradation of creosol, 3-hydroxy-4-methoxy-6-methyl-N-methylaniline was the major compound isolated, providing evidence of a cyanamide radical. Finally, plausible pathways to the formation of Superoxide anion and cyanamide oxidation products from alkaline hydrogen peroxide and cyanamide are proposed and their impact on delignification is discussed.