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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 6, 1976 - Issue 6
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Original Articles

The Synthesis of Thiol Esters with Dicyclohexylcarbodiimide

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Pages 453-455 | Received 01 Jun 1976, Published online: 06 Dec 2006
 

Abstract

The synthesis of thiol esters from carboxylic acids and thiols is a vexing problem because the equilibrium constants for the reactions are very small.1 The reagent dicyclohexyl-carbodiimide (DCC) is reported to cause the esterification of 2-pyridinethiol with a variety of carboxylic acids2 and the polymerization of thioglycolic acid.3 The purpose of this research was to explore the scope and limitations of the reaction. This method is advantageous when it is not practical to convert the acid to an acid chloride and when it is necessary to avoid strong acids or strong bases such as tertiary amines. An example of the first situation is the thioesterification of d3-acetic acid.

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