The Journal of organic chemistry

Effect of substituent on regioselectivity and reaction mechanism in aminolysis of 2, 4-dinitrophenyl X-substituted benzenesulfonates

IH Um, JY Hong, JA Seok

文献索引：Um, Ik-Hwan; Hong, Jin-Young; Seok, Jin-Ah Journal of Organic Chemistry, 2005 , vol. 70, # 4 p. 1438 - 1444

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被引用次数: 65

摘要

We report on a kinetic study for the nucleophilic substitution reactions of 2, 4-dinitrophenyl X- substituted benzensulfonates (X= 4-MeO, 1a, and X= 4-NO2, 1c) with a series of primary amines in 80 mol% H2O/20 mol% DMSO at 25.0° C. The reactions proceed through SO and CO bond fission pathways competitively. The fraction of the SO bond fission increases as the attaching amine becomes more basic and the substituent X changes from 4-MeO to 4- ...