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Issue 0, 1973
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Participation of o-carboxylate groups in aromatic nucleophilic substitution

Abstract

2-Chloro-3,5-dinitrobenzoicacid (1a) reacts with phenols and alcohols in pyridineto give aryl and alkyl 3,5-dinitrosalicylates (2; R = aryl or alkyl), exclusively in most cases, and along with aryl 2-aryloxy-3,5-dinitrobenzoates (5; R1= R2= aryl) in a few cases. Methyl 2-chloro-3,5-dinitrobenzoate (1b) furnishes methyl 2-aryloxy-3,5-dinitrobenzoates (5; R1= Me, R2= aryl) and aryl salicylates (2; R = aryl). The formation of the aryl salicylates must involve participation of the o-carboxy and o-alkoxycarbonyl groups. The β-lactone (8) and the ortho-ester (14) are suggested as intermediates to explain the observed acylations.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1973, 2949-2956
Article type
Paper

Participation of o-carboxylate groups in aromatic nucleophilic substitution

R. Muthukrishnan, R. Kannan and S. Swaminathan, J. Chem. Soc., Perkin Trans. 1, 1973, 2949
DOI: 10.1039/P19730002949

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