Grignard Reaction and Products. V. Reduction of Ketoximes to Aziridines with Grignard Reagents

抄録

For the purpose of expanding our former finding that cyclohexylmagnesium chloride acted as reductive reagent to convert a ketoxime to an aziridine, following ten ketoximes were treated with cyclohexylmagnesium chloride or isobutylmagnesium bromide : Oximes (4-13) of dibenzyl ketone, phenyl benzyl ketone, 2-benzhydrylcyclohexanone, 2-benzoylcyclohexanone, 2-(1-phenyl) cyclohexylcyclohexanone, propiophenone, 4-phenyl-4-methyl-pentan-2-one, cyclohexanone, benzophenone and camphor. By this treatment, ketoximes (4-10) suffered reduction to be converted to aziridines. Among those, the cases of 9 and 10 were accompanied with Hoch-Campbell reaction. 12 and 13 were converted to ketimines by the same treatment.