M. Elinson, A. Dorofeev, Sergey K. Feducovich
Aug 21, 2006
Citations
1
Influential Citations
15
Citations
Journal
Tetrahedron
Abstract
Abstract Indirect electrochemical oxidation of 1-N-subsituted piperidin-4-ones in methanol in an undivided cell in the presence of sodium iodide/sodium methoxide system leads to the corresponding α-hydroxyketals in 50–80% substance yield (50–65% current yield). 2,2,6,6-Tetramethylpiperidin-4-one under the same conditions forms a mixture of methyl 2,2,5,5-tetramethyl-3-pyrrolidinecarboxylate and methyl 2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylate in 70% substance yield (60–70% current yield) via electrochemically induced Favorskii rearrangement.