Results are presented from the first study of the effect such organic inhibitors of radical reactions as p-cumylphenol, 2,6-di-tert-butyl-4-methylphenol (ionol), 2,2,6,6-tetramethylpiperidine, 2,2,6,6tetramethylpiperidine-1-oxyl, and elemental sulfur have on the formation of ferrous didodecanethiolate [Fe(SDd) 2 ] in the reaction between dodecanethiol (DdSH) and metallic iron with mechanochemical activation in polar and nonpolar solvents, such as hexane, dibutyl disulfide, 3-heptene, styrene, and ethanol. A previously unknown tribochemical reaction of DdSH and pyrite is revealed.