Studies of Tertiary Amine Oxides. Part 13. Solvent Effects on the Rate of Thermal Rearrangement of N-(2,4-Dinitrophenyl)piperidine N-Oxide
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 reasonably 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.
Khuthier, Abdul-Hussain,Hanna, Salim Y.,Al-Mallah, Khawla Y.
Arylamines constitute the core structure of many therapeutic agents, agrochemicals, and organic materials. The development of methods for the efficient and selective construction of these structural motifs from simple building blocks is desirable but stil
Svejstrup, Thomas D.,Ruffoni, Alessandro,Juliá, Fabio,Aubert, Valentin M.,Leonori, Daniele
supporting information
p. 14948 - 14952
(2017/11/20)
Studies of Tertiary Amine Oxides. Part 14. Protic Solvent Effects on the Rate of Thermal Rearrangement of N-(2,4-Dinitrophenyl)piperidine N-oxide
The rate of rearrangement of N-(2,4-dinitrophenyl)piperidine N-oxide has been studied in 15 hydroxylic solvents.The first-order rate coefficients (kobs) have been successfully correlated with different solvent parameters.The results are explained in terms of the nucleophilic solvation capability of the solvent which in turn supports the previously proposed three-membered ring-activated complex.Moreover, the role of the HBD ability of the solvent in this reaction is also pronounced, particularly since reaction in alcohols exhibits lower reactivity and higher enthalpy and entropy of activation compared with aprotic solvents.
Studies of Tertiary Amine Oxides. Part 8. Rearrangement of N-(2,4-Dinitrophenyl)-piperidines and -morpholine N-Oxides in Aprotic Solvents
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
Khuthier, Abdul-Hussain,Al-Mallah, Khawla Y.,Hanna, Salim Y.
p. 109 - 112
(2007/10/02)
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