N-Lithium derivatives of aliphatic amines in the synthesis of 1-alkyl-2-phenyldiazene 2-oxides

Magnesium derivatives of aliphatic amines containing α-hydrogen atoms, in contrast to t-BuNHMgBr, do not form phenylaliphatic diazene oxides upon reaction with nitrobenzene, but rather reduce it to azobenzene and azoxybenzene. Asymmetric diazene oxides are formed when the magnesium derivatives are replaced by lithium derivatives. The reaction of t-BuNHLi with dimethylnitramine gives 1,3,5-trimethyl-1,3,5-triazacyclohexane.