5457-37-4Relevant articles and documents
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.
