The Stable Alkylation Products of Organonitrosohydroxylamines

The stable alkylation products of alkyl and aryl nitrosohydroxylamines seem to exist in a hitherto unknown structure, the diimide dioxide linkage. The alternative possibility is the alkyl diazotate monoxide structure, but the latter cannot account for the pure methane evolved when the substances are treated with methyl halide Grignard reagent. The principal products of this reaction with Grignard reagents are diimide monoxides formed subsequently by addition of an equivalent of reagent with elimination of the original alkoxy group as its magnesium salt. Nitration of N-methyl-N′-phenyldiimide dioxide shows that in salt-forming media (nitric-sulphuric) the N2O2R group is electrically negative, but dipole moment studies show that it is highly degenerate. This resonance stabilization is not unexpected in view of the high stability of the diimide dioxides in acidic media.