Regioselective Hydrolysis and Transesterification of Dimethyl 3-Benzamidophthalates Assisted by a Neighboring Amide Group

Autor:	Janez Košmrlj, Franc Perdih, Marko Krivec, Marijan Kočevar
Rok vydání:	2016
Předmět:	chemistry.chemical_classification 010405 organic chemistry Carboxylic acid Organic Chemistry Regioselectivity Transesterification 010402 general chemistry 01 natural sciences 0104 chemical sciences Hydrolysis chemistry.chemical_compound chemistry Amide Pyridine Organic chemistry Moiety Selectivity
Zdroj:	The Journal of Organic Chemistry. 81:5732-5739
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.6b00765
Popis:	An efficient, highly regioselective hydrolysis and transesterification of dimethyl 3-benzamidophthalates into the corresponding carboxylic acid monoesters and mixed esters (including tert-butyl esters) under basic conditions is presented. The selectivity is governed by the neighboring 3-benzamido moiety's participation and by the nature of the solvent. In alcohols the reaction occurred exclusively at the ortho-position to the benzamido functionality, in pyridine or acetonitrile at both ester groups. An insight into the mechanistic pathway was obtained from a (1)H NMR study in perdeuteromethanol.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::92db424b468733910f2c9966544aacae https://doi.org/10.1021/acs.joc.6b00765 Zobrazit plný text záznamu