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Nucleophilic Acyl Substitution via Aromatic Cation Activation of Carboxylic Acids: Rapid Generation of Acid Chlorides under Mild Conditions

David J. Hardee, Lyudmila Kovalchuke and Tristan H. Lambert*

*Department of Chemistry, Columbia University, New York, New York 10027, Email: tl2240columbia.edu

D. J. Hardee, L. Kovalchuke, T. H. Lambert, J. Am. Chem. Soc., 2010, 132, 5002-5003.

DOI: 10.1021/ja101292a (free Supporting Information)


Abstract

The conversion of carboxylic acids to their corresponding acid chlorides occurs rapidly in the presence a tertiary amine base and 3,3-dichlorocyclopropenes via aromatic cation-activated nucleophilic acyl substitution. The effect of cyclopropene substituents on the rate of conversion is examined. Conditions were developed for the preparation of acid sensitive acid chlorides.

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Key Words

amides, acyl chlorides


ID: J48-Y2010-0910