147357-85-5Relevant academic research and scientific papers
A reversible safety-catch method for the hydrogenolysis of N-benzyl moieties
Johnson II, David C.,Widlanski, Theodore S.
, p. 8483 - 8487 (2007/10/03)
The benzyl groups of β-hydroxy-N-benzyl sulfonamides are labile toward hydrogenolysis-unlike N-benzyl sulfonamides lacking the β-hydroxy moiety. We find that N-acyl-N-benzyl sulfonamides undergo hydrogenolysis under very mild conditions. Based upon these observations, we developed a reversible safety-catch method using tert-butoxycarbonyl moieties to activate N-benzyl sulfonamides toward hydrogenolysis. We also explored the utility of the safety-catch activation method for other nitrogen-based functionality such as N-benzyl carboxamides, imides, and related functionality.
Selective Cathodic Cleavage of Unsymmetrical Imidodicarbonates, Acylcarbamates and Diacylamides
Maia, Hernani L. S.,Monteiro, Luis S.,Degerbeck, Fredrik,Grehn, Leif,Ragnarsson, Ulf
, p. 495 - 500 (2007/10/02)
A study of the selective cathodic cleavage of one of the alkoxycarbonyl or acyl groups from various imidodicarbonates, acylamides, and diacylamides is reported.The compounds investigated include all 15 possible combinations of the following groups in unsymmetrical N,N-diprotected derivatives of benzylamine: p-nitrobenzyloxycarbonyl, trichloroethyloxycarbonyl, toluene-p-sulfonyl, benzoyl, benzyloxycarbonyl, and tert-butyloxycarbonyl which can all be electrochemically cleavaged, except the last one.Initially the compounds were examined by cyclic voltammetry in order to measure the potentials associated with the cleavage of each group and afterwards they were electrolysed at constant potential in the presence of a proton donor.The following ranges in negative potential were recorded: 1.03-1.13 V , 1.8-2.14 V (Troc), 1.75-2.41 V (Tos), 1.88-2.52 V (Bz), and 2.83-2.9 V (Z), thus occasionally revealing a drastic effect of the auxiliary group.In the eletrolytic experiments competitive attack by base occasionally led to mixtures of monoacylamides.However, all compounds apart from some of the trichloroethyloxycarbonyl derivatives could be selectively cleaved in 89-100percent yields when an appropriate proton donor was used.Tentative explanations are given for the behaviour of the compounds studied and some conclusions are drawn.
