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DOI: 10.1055/a-1472-7578
N-p-Toluenesulfinylimidazole: A New in situ Reagent for the Mild and Efficient Synthesis of p-Toluenesulfinate Alkyl Esters and Aryl Esters
Acknowledgment is made to the National Science Foundation (NSF) for SC-XRD (CHE-1039689) analyses from Departmental instrumentation obtained from the Major Research Instrumentation (MRI) program.
Abstract
A new synthetic methodology has been developed for the synthesis of sulfinate alkyl and aryl esters. The methodology involves the combination of p-toluenesulfinic acid and 1,1′-carbonyldiimidazole (CDI) to create the putative reagent sulfinylimidazole. The process spontaneously releases carbon dioxide upon the addition of the CDI to the acid suggesting the rapid formation of the proposed reagent. Reaction of this reagent with a series of alcohols (primary, secondary, and tertiary) afforded the corresponding sulfinate alkyl esters in good to excellent yields by the addition of alcohols. It was also possible to form the related sulfinate aryl esters by treating the proposed sulfinylimidazole with selected phenols (phenol, p-tert-butylphenol, and thymol). The aryl esters were formed in excellent conversion based on analysis of the 500 MHz 1H NMR spectra of the crude reaction mixtures.
Keywords
sulfinate ester - sulfinate aryl ester - p-toluenesulfinic acid - 1,1′-carbonyldiimidazole - sulfinylimidazoleSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1472-7578. 1H and 13C NMR spectroscopic data, and X-ray crystallographic data for 21a, are included.
- Supporting Information
Publication History
Received: 09 March 2021
Accepted after revision: 01 April 2021
Accepted Manuscript online:
01 April 2021
Article published online:
19 April 2021
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