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.
The conversion of carboxylic acids to their corresponding acid chlorides occurs rapidly in the presence of 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.
see article for more examples