Oxidation of N-benzylidenebenzylamine by oxygen through the formation of a carbanion

A study was carried out on the oxidation of the methylene group of N-benzylidene-benzylamine through the formation of a carbanion. The conditions were found for a combined oxidation-reduction process using KOH, O/sub 2/, solvent, dibenzo-18-crown-6 and NaBH/sub 4/, in which the oxidation is shifted toward the formation of a hydroxy compound, namely, N-benzylidene-2-hydroxybenzylamine. Oxidation in this system is a convenient preparative method for introducing a hydroxyl group into acidic CH bonds.