111013-03-7Relevant academic research and scientific papers
UNEXPECTED ELECTROOXIDATIONS OF AROMATIC ENOL ETHERS IN THE PRESENCE OF NON CURRENT NUCLEOPHILES.
Cariou, Michel,Simonet, Jacques,Toupet, Loic
, p. 1275 - 1276 (1987)
The electrooxidation of aromatic enol ethers can lead to unexpected substitution or additions by non current nucleophiles.For instance, the oxidation in the presence of lutidine leads exclusively to the corresponding N-substituted lutidinium salts whereas
Comportement anodique particulier d'alkyl (aryl) oxy-1 triaryl-1,2,2 ethylenes, en presence de bases solubles et insolubles
Cariou, Michel
, p. 1015 - 1021 (2007/10/02)
The electrooxidation of 1-alkyl (aryl) oxy-1,2,2-triarylethylenes, with LiClO4 as supporting electrolyte, led to unexpected compounds resulting from the reaction of electrogenerated species on the base added in the anodic compartment.Thus, 1-methoxy-1,2,2-triphenylethylene 1a, by electrooxidation in acetonitrile, in the presence of 2,6-lutidine, led exclusively to an N-aryl substituted pyridinium perchlorate 6a.On the other hand, the expected methoxy-ketone 4 was mainly formed if the electrooxidation was carried out in the presence of either 2,6-di-tert-butyl-4-methyl-pyridine or K2CO3, or else if the phenyl groups are methoxylated in the para position (compound 1b).The 1-phenoxy-1,2,2-triphenyl-ethylene 2 led to the same results, whereas a cyclization reaction could have been expected.In the same way, the corresponding non-alkoxylated product, 1,1,2-triphenyl-ethylene 3, by electrooxidation in the presence of 2,6-lutidine, led to an N-vinyl substituted lutidinium perchlorate 10.In methanol, in the presence of K2CO3, the electrooxidation of enol ether 1a led to the mixture of the expected dimethoxylated product 11 and dioxolane 12; in the presence of 2,6-lutidine, dimethoxylation of the ethylenic double bond is accompanied by partial para-methoxylation of an aromatic ring that led to compound 13.
