Premium
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.