The Zelinsky Institute continues research on the diacetyliminoxyl radical synthesized for the first time at the Institute

The field of free radical reagents in organic chemistry has long been associated almost exclusively with aminoxyl radicals, mainly 2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) and its analogs. Diacetyliminoxyl is the first synthetically readily available oxime radical, obtained for the first time at the Zelinsky Institute, and differs sharply from aminoxyl radicals in structure and reactivity. It has outstanding self-degradation resistance compared to other sterically unhindered oxime radicals. In one of the recent studies by scientists from the Laboratory for the Study of Homolytic Reactions of the ZIOC, diacetyliminoxyl was used as a new radical reagent for organic synthesis. Its use has been demonstrated in oxidative functionalization with cleavage of OH, CH, NH and SH bonds and in dehydrogenation processes. It was found that diacetyliminoxyl was a highly selective reagent that abstracts a hydrogen atom from the most activated substrates or functional groups. Diacetyliminoxyl has also been shown to be an exceptionally effective scavenger of stabilized and sterically hindered C-radicals, which are not scavenged by the typical free radical scavenger like TEMPO.
 

Source:

Alexander S. Budnikov, Igor B. Krylov, Ilya V. Kuzmin, Oleg O. Segida, Andrey V. Lastovko, Mikhail I. Shevchenko, Gennady I. Nikishin, Alexander O. Terent'ev Diacetyliminoxyl as a Selective Radical Reagent for Organic Synthesis: Dehydrogenation and Dehydrogenative C–O Coupling Reactions // Org. Chem. Front. 2023, 10, 388-398. DOI: 10.1039/D2QO01649D.