Reactions of nitroanisoles. Part 6. Reaction of 2,6-dinitroanisole with cyclohexylamine in mixed solvents. Solvent evidence for the ‘dimer’ mechanism

Abstract

The reaction of 2,6-dinitroanisole with cyclohexylamine in methanol and benzene–methanol was studied at several amine concentrations. Although the reaction rate in methanol is higher than in benzene, addition of small amounts of methanol to the benzene solution diminishes the rate of reaction (which is of third order in amine), reaching a minimum value at nearly 30% methanol, after which the rate increases almost linearly with the methanol content. These and other results, here described, are satisfactorily explained by a previously proposed reaction scheme, in which the dimer of the amine is operating.