Sopped-Flow Kinetics of 1-Ethoxy-2,4-dinitronaphthalene with Pyrrolidine and Piperidine in Dimethyl Sulfoxide Solution

Article abstract of DOI:10.1246/bcsj.62.1969

The reaction of 1-ethoxy-2,4-dinitronaphthalene (1) with pyrrolidine or piperidine in dimethyl sulfoxide occured in two stages (Stages I and II).In the stage I, a ?-adduct forms at such a rate as is measured by a stopped-flow technique, and in the stage II it decays at a slower and spectrophotometrically measurable rate.The pyrrolidine system is more reactive than the piperidine system in the stages I and II, with the former reactivity in the stage II being ca. 11000 times higher than the latter.This huge difference was found by NMR evidence to stem from the structure of transition state in the stage II.Further, the activation parameters were determined, which corresponded to such difference in reactivity very well.