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

Shahrokhian, S ; Sharif University of Technology

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  1. Type of Document: Article
  2. DOI: 10.1007/s10800-009-9987-y
  3. Abstract:
  4. 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
  5. Keywords:
  6. Catechols ; Controlled-potential coulometry ; Mercapto thiadiazole ; Michael addition ; 4-methylcatechol ; Aqueous medium ; Electro-synthesis ; Electrochemical behaviors ; Electrochemical synthesis ; Electrogeneration ; Glassy carbon electrodes ; Michael additions ; Michael-type reaction ; Oxidation mechanisms ; Reaction products ; Spectrometric methods ; Thiadiazoles ; Voltammetric ; Addition reactions ; Glass membrane electrodes ; Glassy carbon ; Phenols ; Reaction intermediates ; Spectrophotometers ; Spectrophotometry ; Synthesis (chemical) ; Cyclic voltammetry
  7. Source: Journal of Applied Electrochemistry ; Volume 40, Issue 1 , 2010 , Pages 115-122 ; 0021891X (ISSN)
  8. URL: http://link.springer.com/article/10.1007%2Fs10800-009-9987-y