A novel approach towards dethioacetalization reactions with H2O2–SOCl2 system

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Abstract

A simple and efficient protocol for the deprotection of dithioacetal, 1,3-dithianes and 1,3-dithiolanes has been developed using H2O2–SOCl2 reagent system. In addition to the absence of overoxidation products for oxidation-prone substrates, high chemoselectivity, the low cost and availability of the reagents, simplicity of the method, short reaction times, and excellent yields can also be considered as strong points for this method.

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General

Thionyl chloride (SOCl2) and hydrogen peroxide (30%) are commercial products (Merck Chemical Company) and were used without further purification. Thioacetals and thioketals were prepared according to reported procedures [20]. Melting points were determined in a capillary tube and are not corrected. 1H NMR spectra were recorded on a Bruker 200 spectrometer using TMS as internal standard. IR spectra were recorded on a Shimadzu IR-470 spectrophotometer using KBr pellets.

General procedure for dethioacetalization with H2O2–SOCl2 reagent system

A mixture of thioacetal (2 

Acknowledgment

We are thankful to the Razi University Research Council for partial support of this work.

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    Citation Excerpt :

    A variety of methods for deprotection of dithioacetals to carbonyl compounds have been developed to date [274–292]. Bahrami et al. [272] demonstrated that the thioacetals can be deprotected to afford carbonyl groups using H2O2–SOCl2 reagent system (Scheme 145). The excellent yields, high chemoselectivity, short reaction times, mild conditions, the availability and low cost of the reagents and simplicity of the method are the advantages of this approach.

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