20455-68-9Relevant articles and documents
A General, Selective, High-Yield N-Demethylation Procedure for Tertiary Amines by Solid Reagents in a Convenient Column Chromatography-like Setup
Rosenau, Thomas,Hofinger, Andreas,Potthast, Antje,Kosma, Paul
, p. 541 - 544 (2004)
(Equation presented) A traditional preparative chromatographic column can be used to achieve quantitative N-demethylation of tertiary N-methylamines and alkaloids. The filling is the crucial part and is loaded with different solid reagents in three reaction zones. The parent compound is charged on the column, and the neat N-demethylated secondary amine leaves the column some minutes later.
Diaz, Carlos
, p. 655 - 658 (1986)
Selenoxide elimination triggers enamine hydrolysis to primary and secondary amines: A combined experimental and theoretical investigation
Bortoli, Marco,Gianoncelli, Alessandra,Ongaro, Alberto,Orian, Laura,Oselladore, Erika,Ribaudo, Giovanni,Zagotto, Giuseppe
, (2021/05/26)
We discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimination products of such compounds, paving the way for a novel strategy to selectively release bioactive molecules. The underlying mechanism was investigated using NMR, mass spectrometry and density functional theory (DFT).
Computationally forecasting the effect of dibenzylammonium substituents on pseudorotaxane formation with dibenzo[24]crown-8
Payne, Nicholas A.,Delmas, Luke C.,McDowell, Sean A.C.,Williams, Avril R.
supporting information, p. 5175 - 5179 (2015/08/18)
The ability to predict the relative stabilities of analogous pseudorotaxanes is essential for the synthetic chemist yet simplified computational forecasting approaches remain scarce. Consequently, ten [2]pseudorotaxanes have been assembled (from a series of para-substituted dibenzylammonium ions and dibenzo[24]crown-8) and their experimentally-determined stabilities correlated with two computational parameters closely related to complexation energy. The strongest relationship was obtained from density functional theory calculation of binding energy (R2 = 0.92) while determination of the maximum surface electrostatic potential on the dibenzylammonium ions (a proxy indicator of complex stability) afforded comparable results (R2 = 0.88) with great reduction in computational expense.