Treatment of nucleophilic arenes with N,N-dimethyl-2-imidazolidinone O-methoxyacetyloxime and SnCl4 produced the corresponding N-arylimines, which were converted to anilines by hydrolysis with CsOH and to N-methylanilines by LiAlH4 reduction.
2-Imidazolidinone O-sulfonyloxime reacts with various aryl and alkyl Grignardreagents as an electrophilic amination reagent, giving N-alkylated imines. The resulting imines are transformed to primaryamines and N-methyl secondary amines by hydrolysis with CsOH and LiAlH4 reduction, respectively.