Studies of tertiary amine oxides. Part 8. Rearrangement of N-(2,4-dinitrophenyl)-piperidines and -morpholine N-oxides in aprotic solvents

Abstract

The N-oxides of N-(2,4-dinitrophenyl)-piperidines and -morpholine undergo thermal rearrangement to the substituted hydroxylamines. The kinetics of the rearrangement were studied in aprotic solvents at four or five temperatures. Steric and polar factors have great influence on the rate of rearrangement. The kinetic results together with cross-over experiments are in full agreement with an intramolecular cyclic mechanism (S_Ni).