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Green Oxidation of Aromatic Hydrazide Derivatives Using an Oxoammonium Salt
Nidheesh Phadnis1, Jessica A Molen1, Shannon M Stephens2
1Department of Biological and Chemical Sciences, College of Life Sciences, Thomas Jefferson University, 4201 Henry Ave, Philadelphia, Pennsylvania 19144, United States.
Abstract:
Aromatic diazenes are often prepared by oxidation of the corresponding hydrazides using stoichiometric quantities of nonrecyclable oxidants. We developed a convenient alternative protocol for the oxidation of aromatic hydrazides using Bobbitt's salt (1), a metal-free, recyclable, and commercially available oxoammonium reagent. A variety of aryl hydrazides were oxidized within 75 min at room temperature using the developed protocol. Computational insight suggests that this oxidation occurs by a polar hydride transfer mechanism.
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