Anodic oxidation of mono- and disubstituted 1,4-dimethoxybenzenes

Cheng Chu Zeng, James Y. Becker

Research output: Contribution to conferencePaperpeer-review

Abstract

The electrochemical oxidation of mono- and disubstituted 1,4-dimethoxybenzene derivatives with no, one and two benzylic CH2X groups (X= OAc, Cl, OH) (5a-c and 6a-c) has been carried out under different experimental conditions. Constant-current electrolysis in KOH-methanol solutions afforded mostly the corresponding 1,4-quinone derivatives from 5a-c and 6b, whereas the disubstituted 1,4-dimethoxybenzenes 6a,c underwent side-chain oxidation to form 2,5-dimethoxyterephthalaldehydes. Upon altering the commonly used basic medium to neutral LiClO4-methanol, novel coupling products from un-and mono-substituted substrates, and quinone derivatives from disubstituted ones were formed. Controlled-potential oxidation at glassy carbon anodes and in a neutral LiClO4-methanol medium led to polymeric products in addition to new coupling ones from mono-substituted substrates, and quinones and side-chain oxidation (or substitution) products from the disubstituted ones.

Original languageEnglish
Pages145-148
Number of pages4
StatePublished - 1 Dec 2004
EventAnalytical, Mechanistic, and Synthetic Organic Electrochemistry - The Sixth International Manuel M. Baizer Symposium in Honor of Dennis H. Evans and Masao Tokuda - San Antonio, TX, United States
Duration: 9 May 200414 May 2004

Conference

ConferenceAnalytical, Mechanistic, and Synthetic Organic Electrochemistry - The Sixth International Manuel M. Baizer Symposium in Honor of Dennis H. Evans and Masao Tokuda
Country/TerritoryUnited States
CitySan Antonio, TX
Period9/05/0414/05/04

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