November 18, 1988

Electrochemical amide oxidations in the presence of monomethoxylated phenyl rings. An unexpected relationship between the chemoselectivity of the oxidation and the location of the methoxy substituent

Kevin D. Moeller, Sharif Tarazi, Mohammad R Marzabadi

Tetrahedron Lett., 1989, 30(10), 1213-1216

The chemoselectivity of electrochemical amide oxidations in the presence of monomethoxylated phenyl rings was examined. Oxidation of (3-methoxyphenyl)acylpyrrolidine led to exclusive formation of the desired amide oxidation products, while oxidation of the 4-methoxyphenyl isomer led to exclusive formation of aromatic ring oxidation products.

The chemoselectivity of electrochemical amide oxidations in the presence of monomethoxy phenyl rings was found to be completely dependent on the position of the methoxy substituent.