Substituent effects on the decarboxylation of dinitrobenzoate ions. Representative aromatic SE1 reactions

P Segura, JF Bunnett, L Villanova

Index: Segura, Pascual; Bunnett, Joseph F.; Villanova, Laura Journal of Organic Chemistry, 1985 , vol. 50, # 7 p. 1041 - 1045

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Citation Number: 24

Abstract

Results Synthesis of Substrates. Most of the desired dinitrobenzoic acid derivatives, although previously unknown, were accessible by chromic acid oxidation of the corresponding substituted toluenes. However, oxidation of 4-methoxy-2, 6-dinitrotoluene was unsatisfactory. Accordingly, acid Io was obtained by an alternative approach, namely, the reaction of sodium methoxide with methyl 2, 4, 6-trinitrobenzoate (VI) to effect ...