Electrochemical study of catechols in the presence of 2-thiazoline-2-thiol: application to electrochemical synthesis of new 4,5-dihydro-1,3-thiazol-2-ylsulfanyl-1,2-benzenediol derivatives

Electrochemical oxidation of catechols ( 1a – d ) has been studied in the presence of 2-thiazoline-2-thiol ( 3 ) as a nucleophile in aqueous solution, using cyclic voltammetry and controlled potential coulometry. The results indicate that the quinones derived from catechols ( 1a – d ), participate i...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of applied electrochemistry 2008-12, Vol.38 (12), p.1743-1747
Hauptverfasser: Fakhari, A. R., Hosseiny Davarani, S. S., Ahmar, H., Makarem, S.
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Electrochemical oxidation of catechols ( 1a – d ) has been studied in the presence of 2-thiazoline-2-thiol ( 3 ) as a nucleophile in aqueous solution, using cyclic voltammetry and controlled potential coulometry. The results indicate that the quinones derived from catechols ( 1a – d ), participate in Michael addition reactions with 2-thiazoline-2-thiol and via an EC mechanism pathway, convert to the corresponding catechols derivatives ( 4a – d and 4 ′ d ). The electrochemical synthesis of compounds ( 4a – d and 4 ′ d ) has been successfully performed at a carbon rod electrode and in an undivided cell with good yield and high purity. The products have been characterized by IR, 1 H NMR, 13 C NMR and MS.
ISSN:0021-891X
1572-8838
DOI:10.1007/s10800-008-9625-0