Aminolysis of O-aryl thionobenzoates: amine basicity combines with modulation of the nature of substituents in the leaving group and thionobenzoate moiety to control …

…, SJ Hwang, S Yoon, SE Jeon, SK Bae

文献索引：Um, Ik-Hwan; Hwang, So-Jeong; Yoon, Sora; Jeon, Sang-Eun; Bae, Sun-Kun Journal of Organic Chemistry, 2008 , vol. 73, # 19 p. 7671 - 7677

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被引用次数: 67

摘要

A kinetic study is reported for aminolysis of OY-substituted phenyl thionobenzoates (1a− f) and O-4-nitrophenyl X-substituted thionobenzoates (2a− f) in 80 mol% H2O/20 mol% DMSO at 25.0±0.1° C. The reaction proceeds through one or two intermediates (ie, a zwitterionic tetrahedral intermediate T±and its deprotonated form T−) depending on the basicity difference between the nucleophile and nucleofuge, that is, the reaction proceeds through ...