Reactions of Nitroanisoles. 4. Reaction of 2,4- and 2,6-Dinitroanisole with Cyclohexylamine. Evidence of a "Dimer" Nucleophile

Article abstract of DOI:10.1021/jo00158a007

The reactions of 2,4- and 2,6-dinitroanisole (DNA) with cyclohexylamine in benzene and in cyclohexane were studied at three temperatures.Two unusual facts were observed: the overall reaction rate is of third order with respect to the amine concentration, and an inverse temperature effect is found for the reaction of 2,4-DNA in cyclohexane.Both experimental findings and some other "anomalous" results reported in the literature are satisfactorily accommodated in a reaction scheme in which the dimer of the amine is operating.