Selective synthesis of oximes with primary aliphatic amines and hydrogen peroxide in the presence of catalytic quantities of titanium silicalite molecular sieves

Abstract

Primary aliphatic amines with α-hydrogen atoms are oxidized in the presence of hydrogen peroxide as oxidant and catalytic quantities of titanium silicalite molecular sieves to give the corresponding oximes as the main products; the latter are formed with good substrate selectivity and peroxide efficiency. Since the substrate dimensions allow an intracrystalline reaction, by-products, which become significant for larger substrates, are determined by steric constraints in the intracrystalline voids rather than by reaction of electrophilic oxygen with carbon of increased nucleophilicity.