Mechanistic Insights into the Reductive N-O Bond Cleavage of <i>O</i>‑Acyl Hydroxylamines: Dual Reactivity as Potent Oxidants and Nitrogen Transfer Agents.

ABSTRACT: Hydroxylamine (NH₂OH), an N-O containing moiety and a pivotal intermediate in the nitrogen biogeochemical cycle, typically functions under reducing conditions, in stark contrast to its isoelectronic O-O analogue, hydrogen peroxide (H₂O₂). Oxygen-substituted hydroxylamine derivatives, widely employed in organic synthesis, utilize electron-withdrawing substituents (R) to weaken the N-O bond, thereby enabling the generation of reactive "N-transfer" intermediates. Although these reagents are increasingly recognized for their dual roles as masked "amine" donors and potential "oxidants", direct experimental validation of their oxidative capacity has remained elusive. Herein, we report a detailed mechanistic investigation integrating kinetic, spectroscopic, electr

SUBMITTER: Bishnoi P 

PROVIDER: S-EPMC12492043 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature