Participation of o-carboxylate groups in aromatic nucleophilic substitution

Muthukrishnan, R. ; Kannan, R. ; Swaminathan, S. (1973) Participation of o-carboxylate groups in aromatic nucleophilic substitution Journal of the Chemical Society, Perkin Transactions 1, 1973 . pp. 2949-2956. ISSN 0300-922X

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Official URL: http://pubs.rsc.org/en/content/articlelanding/1973...

Related URL: http://dx.doi.org/10.1039/P19730002949

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.

Item Type:Article
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ID Code:70744
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