Studies of tertiary amine oxides. Part 13. Solvent effects on the rate of thermal rearrangement of N-(2,4-dinitrophenyl)piperidine N-oxide
Abstract
The rearrangement of N-(2,4-dinitrophenyl)piperidine N-oxide was studied in ten aprotic solvents. Different correlations of the first-order rate coefficients (kobs.) with several solvent parameters were examined for the ten solvents with a range of 45 units in dielectric constant; the multiparameter equations of Krygowski and Fawcett, Koppel and Palm, and Kamlet and Taft were all examined. The kobs. values were correlated reasonable well with the Lewis basicity of the solvent. Gutmann's donor number, and Dimroth's ET(30) parameter when hydrogen-bond-donor solvents were excluded.