Oxidative nucleophilic substitution of hydrogen versus ring-opening in the reaction of 4-r-2-nitrothiophenes with amines. The crucial effect of 4-alkyl groups

…, S Morganti, E Rizzato, D Spinelli

Index: Consiglio, Giovanni; Spinelli, Domenico; Gronowitz, Salo; Hoernfeldt, Anna-Britta; Maltesson, Britta; Noto, Renato Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982 , p. 625 - 630

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Citation Number: 21

Abstract

4-Alkyl-2-nitrothiophenes [10: R= CH3, CH (OH) CH3, CH (OCH3) CH3] react with secondary aliphatic amines, in the presence of AgNO3, to give 3-alkyl-2-amino-5- nitrothiophenes (12) through an oxidative nucleophilic substitution of hydrogen (ONSH) of