Radical Intermediates In Chloramine and N-Chloroimide Reactions

Abstract

Nitrogen-centered radicals produced by the action of Ag(0) or Ag(I)-amine systems on N-chloroazacyclononane, N-chloropiperidine, and N-chlorosuccinimide have been trapped using 2-methyl-2-nitrosopropane. The resulting nitroxides exhibited e.p.r. spectra consistent with structures 1, 2, and 3. Hydrogen gas evolved during reaction of the chloramines with Ag(0) was shown to arise completely from the amine derivatives.Excess Ag(0) reduced the succinamidyl radical to give the silver salt of succinimide.