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N-p-Toluenesulfinylimidazole: A New in situ Reagent for the Mild and Efficient Synthesis of p-Toluenesulfinate Alkyl Esters and Aryl Esters

Jessica L. Shaw, Brad J. Austermuehle, Jordan M. Witte, Timothy R. Dorsey, Christina Delach, Christopher G. Hamaker, Shawn R. Hitchcock*

*Department of Chemistry, Illinois State University, Normal, IL 61790-4160, USA, Email: hitchcockilstu.edu

J. L. Shaw, B. J. Austermuehle, J. M. Witte, T. R. Dorsey, C. Delach, C. G. Hamaker, S. R. Hitchcock, Synthesis, 2021, 53, 2693-2701.

DOI: 10.1055/a-1472-7578


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Abstract

The reaction of p-toluenesulfinic acid with 1,1′-carbonyldiimidazole (CDI) provides sulfinylimidazoles. The process spontaneously releases carbon dioxide upon addition of CDI to the acid suggesting the rapid formation of the proposed reagent. A subsequent reaction with a series of alcohols (primary, secondary, and tertiary) affords the corresponding sulfinate alkyl esters in very good yields.

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Key Words

sulfinate esters, sulfinate aryl esters, p-toluenesulfinic acid, 1,1'-carbonyldiimidazole, sulfinylimidazole


ID: J66-Y2021