ECEC and ECE‐Type Mechanisms in Electrochemical Oxidation of 4‐Substituted Catechols in the Presence of 4‐Hydroxy‐6‐methyl‐2‐pyrone | Zendy

Nematollahi Davood | Zendy; Forooghi Zinat | Zendy

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ECEC and ECE‐Type Mechanisms in Electrochemical Oxidation of 4‐Substituted Catechols in the Presence of 4‐Hydroxy‐6‐methyl‐2‐pyrone

Author(s) -

Nematollahi Davood,

Forooghi Zinat

Publication year - 2003

Publication title -

electroanalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.574

H-Index - 128

eISSN - 1521-4109

pISSN - 1040-0397

DOI - 10.1002/elan.200302738

Subject(s) - coulometry , quinone , chemistry , decarboxylation , nucleophile , electrochemistry , michael reaction , pyrone , reaction mechanism , aqueous solution , cyclic voltammetry , medicinal chemistry , organic chemistry , photochemistry , catalysis , electrode

Electrochemical oxidation of 3,4‐dihydroxybenzoic acid ( 1 ) and 4‐ tert ‐butylcatechol ( 5 ) in the presence of 4‐hydroxy‐6‐methyl‐2‐pyrone ( 2 ) as nucleophile in aqueous solution has been studied using cyclic voltammetry and controlled‐potential coulometry. The results indicate that 1 via Michael reaction under electro‐decarboxylation reaction converts to heterocyclic compound 4 , and the quinone derived from 4‐ tert ‐butylcatechol ( 5 ) participates in Michael reaction with 2 and through an ECE mechanism converts to the corresponding o ‐quinone ( 6a ). The electrochemical synthesis of 4 and 6a has been successfully performed in an undivided cell.

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