Oxidation of Various Secondary Amines to Imines with N-tert-Butylphenylsulfinimidoyl Chloride

Abstract

Various secondary amines were smoothly oxidized to the corresponding imines at −78 °C by using N-tert-butylphenylsulfinimidoyl chloride and DBU.

A convenient method for the synthesis of nitrones by oxidation of N,N-disubstituted hydroxylamines with N-tert-butylphenylsulfinimidoyl chloride

“…This result indicated that N,N-dialkyl hydroxylamines were oxidized more easily compared to N,N-dialkyl secondary amines which afforded no corresponding ketimines under the same oxidation conditions. 19 In the case of an unsymmetrical hydroxylamine, N-isopropyl-N-(3-phenylpropyl)hydroxylamine 10a, the oxidation took place exclusively at the position of 3-phenylpropyl group, which indicated considerable influence of steric factors on the regioselectivity of the present nitrone synthesis. Similar regioselectivities were reported also in the oxidation of N,N-disubstituted hydroxylamines with mercuric(II) oxide.…”

Photo-Induced Electron Transfer Between a Reactant Molecule and Semiconductor Photocatalyst: In Situ Doping

“…Several oxidation procedures with stoichiometric, toxic, corrosive and expensive oxidants have been reported [51][52][53][54][55][56][57][58]. However, a catalytic system using molecular oxygen as a sole oxidant has been desired [55,[59][60][61][62][63][64].…”

Strategien zur Erforschung neuer Reaktionen

“…(11)]. [41] Bei unsymmetrischen sekundären Aminen tritt die Oxidation selektiv an den benzylischen oder den weniger gehinderten Positionen ein. Auch primäre Amine werden in einer Eintopfreaktion oxidativ zu den entsprechenden Carbonylverbindungen desaminiert.…”