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Title: Acid anhydrides and the unexpected N,N-diethylamides derived from the reaction of carboxylic acids with Ph<inf>3</inf>P/I<inf>2</inf>/Et<inf>3</inf>N
Authors: Wong Phakhodee
Chuthamat Duangkamol
Sirilak Wangngae
Mookda Pattarawarapan
Keywords: Biochemistry, Genetics and Molecular Biology
Pharmacology, Toxicology and Pharmaceutics
Issue Date: 20-Jan-2016
Abstract: © 2015 Elsevier Ltd. All rights reserved. The formation of acid anhydrides from the phosphorous-mediated activation of carboxylic acids was investigated. Under various systems, activation of benzoic acid in the presence of base led to the formation of benzoic anhydride at different rates depending on the reactivity of the reagents. Using the Ph3P-I2/Et3N combination, most aryl acids were converted into the corresponding anhydrides in high yields within 5-10 min. However, for nitro-substituted derivatives, unexpectedly, N,N-diethylamides were isolated without anhydride formation. These results indicated the pronounced effect of substituents in governing these potential side reactions which can significantly affect the yields of acylation reactions promoted by phosphonium species.
ISSN: 18733581
Appears in Collections:CMUL: Journal Articles

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