Document Type
Article
Publication Date
2024
DOI
10.1021/acs.joc.3c02752
Publication Title
Journal of Organic Chemistry
Volume
89
Issue
8
Pages
5841-5845
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.
Rights
Copyright © 2024 The Authors.
This article is licensed under a Creative Commons Attribution 4.0 International (CC BY 4.0) license.
Data Availability
Article states: "The data underlying this study are available in the published article and its Supporting Information."
Original Publication Citation
Phadnis, N., Molen, J. A., Stephens, S. M., Weierbach, S. M., Lambert, K. M., & Milligan, J. A. (2024). Green oxidation of aromatic hydrazide derivatives using an oxoammonium salt. Journal of Organic Chemistry, 89(8), 5841-5845. https://doi.org/10.1021/acs.joc.3c02752
ORCID
0000-0002-8230-2840 (Lambert)
Repository Citation
Phadnis, Nidheesh; Molen, Jessica A.; Stephens, Shannon M.; Weierbach, Shayne M.; Lambert, Kyle M.; and Milligan, John A., "Green Oxidation of Aromatic Hydrazide Derivatives Using an Oxoammonium Salt" (2024). Chemistry & Biochemistry Faculty Publications. 292.
https://digitalcommons.odu.edu/chemistry_fac_pubs/292