N-Nitroso Compounds. Part 6. Oxidation of N-Nitrosodialkylamines by Hydrogen Peroxide in Aqueous Acetic Acid. Effect of Substituents on the Nucleophilicity of the Nitroso Oxygen.

Oxidation of N-nitrosodimethylamine by H2O2-AcOH gave N-nitrodimethylamine in 40% yield, while introduction of an electron-withdrawing substituent into the N-alkyl moiety resulted in a marked decrease in the yield of oxidation product.