Nucleophilic Substitution Reactions of 1-Halogeno-4-COR-2-nitrobenzenes and 1-Halogeno-6-COR-2-nitrobenzenes with Sodium Benzenethiolate and Piperidine. …

…, G Consiglio, V Frenna, D Spinelli

Index: Arnone, Caterina; Consiglio, Giovanni; Frenna, Vincenzo; Spinelli, Domenico Journal of Organic Chemistry, 1997 , vol. 62, # 10 p. 3093 - 3097

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Citation Number: 17

Abstract

A kinetic study of the title reactions has allowed an interpretation of the higher efficiency of an o-carboxamido group with respect to an o-carbomethoxy group in activating the benzenethiolate-dehalogenation reactions in methanol (k CONH2/k CO2Me 2.2-3.0) as due to an interaction between the anionic nucleophile and the hydrogen atoms of the carboxamido group. An inversion of the activating power of the two groups (k CONH2/k ...