Electrophilically catalyzed splitting of dimethoxyamine to methoxynitrenium ion and its reactions

The electrophilically catalyzed splitting of the N-0 bond of dimethoxyamine results in the formation of methoxynitrenium ion, which in reaction with nucleophiles exhibits properties of an ambidentate cation — it methylates rigid nucleophiles and epiminates olefins. The stereospecificity of the addition of the nitrenium ion to cis-2-butene indicates its existence in a singlet electronic ground state.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1384–1389, June, 1990.