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...
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Veröffentlicht in: | Journal of applied electrochemistry 2008-12, Vol.38 (12), p.1743-1747 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
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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. |
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ISSN: | 0021-891X 1572-8838 |
DOI: | 10.1007/s10800-008-9625-0 |