Electrochemical oxidation of pyrrole derivatives in alcoholic medium

• Published in: Collection of Czechoslovak chemical communications Vol. 54; no. 5; pp. 1299 - 1305
• Main Authors: FAROUK TEDJAR, SALAH YMMEL, MIROSLAV JANDA, PETR DUCHEK, HOLY, P, STIBOR, I
• Format: Journal Article
• Language: English
• Published: Praha Czechoslovak Academy of Sciences, Institute of Organic Chemistry and Biochemistry 01-05-1989
• Subjects: Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Preparations and properties; Electrochemical reaction
• ISSN: 0010-0765; 1212-6950
• DOI: 10.1135/cccc19891299

Electrochemical oxidation of pyrrole (
I
), 1-methylpyrrole (
II
), 1,2,5-trimethylpyrrole (
III
), methyl 1-methyl-2-pyrrolecarboxylate (
IV
) and diethyl 3,5-dimethyl-2,4-pyrroledicarboxylate (
V
) has been studied. An advantageous method of preparation of polypyrroles (PP) and conductive PVC-PP composites has been elaborated, permitting a 20 fold starting concentration of the monomer. Electrooxidation of
II
in methanol leads either to 5,5-dimethoxy-1-methyl-3-pyrrolin-2-one (
VII
) or 1-methyl-2,2,5,5-tetramethoxy-3-pyrroline (
VI
), their ratio depending on water content in the alcohol used. Oxidation of
IV
affords the analogous 5-carbomethoxy-5-methoxy-1-methyl-3-pyrrolin-2-one (
X
), oxidation of
III
and
V
leads to products of substitution at the methyl groups.