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Selective synthesis of 4-thiomethyl-1,3-dioxolan-2-ones under microwave irradiation using an environmentally benign KF/Al2O3/PEG-400 system

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Abstract

We describe a simple and rapid method for selective synthesis of 4-thiomethyl-1,3-dioxolan-2-ones promoted by KF/Al2O3 using PEG-400 as solvent under microwave irradiation. The protocol employs 3-O-tosyl glycerol 1,2-carbonate 1 and a diverse array of thiols 2 to afford corresponding 4-thiomethyl-1,3-dioxolan-2-ones 3 in good yield and short reaction time compared with conventional heating methods. Moreover, selective synthesis of 1,3-bis-arylthiopropan-2-ol 4 by a stoichiometric and temperature-controlling reaction is presented.

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Acknowledgments

The authors are grateful to CNPq, FAPERGS, CAPES, and FINEP for financial support.

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Authors and Affiliations

  1. LASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, Pelotas, RS, 96010-900, Brazil

    Gelson Perin, Cristian M. Silva, Elton L. Borges, José E. G. Duarte, Helen A. Goulart, Rafaela B. Silva & Ricardo F. Schumacher

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  1. Gelson Perin
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  2. Cristian M. Silva
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  3. Elton L. Borges
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  4. José E. G. Duarte
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  7. Ricardo F. Schumacher
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Correspondence to Gelson Perin.

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Perin, G., Silva, C.M., Borges, E.L. et al. Selective synthesis of 4-thiomethyl-1,3-dioxolan-2-ones under microwave irradiation using an environmentally benign KF/Al2O3/PEG-400 system. Res Chem Intermed 42, 5873–5885 (2016). https://doi.org/10.1007/s11164-015-2410-x

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  • DOI: https://doi.org/10.1007/s11164-015-2410-x

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