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Investigation of the electrochemical behavior of catechol and 4-methylcatechol in the presence of methyl mercapto thiadiazol as a nucleophile: application to electrochemical synthesis

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Abstract

The present study concerns the electrochemical behavior of catechol and 4-methylcatechol in the presence of 2-mercapto-5-methyl-1,3,4-thiadiazole (MMT) in aqueous medium on the surface of the glassy carbon electrode by means of cyclic voltammetry and controlled-potential coulometry. The oxidation mechanism was deduced from voltammetric and spectrophotometric data. The electro-generation of quinoid intermediates and their subsequent Michael-type reaction with MMT has been investigated as a clean and convenient strategy for the synthesis of corresponding reaction products. In addition, electro-synthesis of Michael addition products has been successfully accomplished by controlled-potential coulometry in a divided H-type cell in mild conditions that can be considered as a green procedure. The reaction products were characterized by spectrophotometric, 1H and 13C NMR, and mass spectrometric methods.

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Acknowledgments

The authors gratefully acknowledge the support of this work by the Research Council and the Center of Excellence for Nanostructures of the Sharif University of Technology, Tehran, Iran.

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Authors and Affiliations

  1. Department of Chemistry, Sharif University of Technology, 11155-9516, Tehran, Iran

    S. Shahrokhian & S. Rastgar

  2. Institute for Nanoscience and Technology, Sharif University of Technology, Tehran, Iran

    S. Shahrokhian

Authors
  1. S. Shahrokhian
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  2. S. Rastgar
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Correspondence to S. Shahrokhian.

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Shahrokhian, S., Rastgar, S. Investigation of the electrochemical behavior of catechol and 4-methylcatechol in the presence of methyl mercapto thiadiazol as a nucleophile: application to electrochemical synthesis. J Appl Electrochem 40, 115–122 (2010). https://doi.org/10.1007/s10800-009-9987-y

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  • DOI: https://doi.org/10.1007/s10800-009-9987-y

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