16891-99-9Relevant articles and documents
Modular Regiospecific Synthesis of Nitrated Fatty Acids
Hock, Katharina J.,Grimmer, Jennifer,G?bel, Dominik,Gasaya, George Gichogo T.,Roos, Jessica,Maucher, Isabelle V.,Kühn, Benjamin,Fettel, Jasmin,Maier, Thorsten J.,Manolikakes, Georg
, p. 615 - 636 (2017)
Endogenous nitrated fatty acids are an important class of signaling molecules. Herein a modular route for the efficient and regiospecific preparation of nitrooleic acids as well as various analogues is described. The approach is based on a simple set of alkyl halides as common building blocks and a Henry reaction/Burgess dehydration sequence for the formation of the key nitroalkene moiety.
Ozone-Mediated Amine Oxidation and Beyond: A Solvent-Free, Flow-Chemistry Approach
Skrotzki, Eric A.,Vandavasi, Jaya Kishore,Newman, Stephen G.
supporting information, p. 14169 - 14176 (2021/06/30)
Ozone is a powerful oxidant, most commonly used for oxidation of alkenes to carbonyls. The synthetic utility of other ozone-mediated reactions is hindered by its high reactivity and propensity to overoxidize organic molecules, including most solvents. This challenge can largely be mitigated by adsorbing both substrate and ozone onto silica gel, providing a solvent-free oxidation method. In this manuscript, a flow-based packed bed reactor approach is described that provides exceptional control of reaction temperature and time to achieve improved control and chemoselectivity over this challenging transformation. A powerful method to oxidize primary amines into nitroalkanes is achieved. Examples of pyridine, C-H bond, and arene oxidations are also demonstrated, confirming the system is generalizable to diverse ozone-mediated processes.
Facile reduction of nitroarenes into anilines and nitroalkanes into hydroxylamines via the rapid activation of ammonia· borane complex by supported gold nanoparticles
Vasilikogiannaki, Eleni,Gryparis, Charis,Kotzabasaki, Vasiliki,Lykakis, Ioannis N.,Stratakis, Manolis
supporting information, p. 907 - 911 (2013/05/08)
Gold nanoparticles supported on titania catalyse, even at a ppm loading level, the quantitative reduction of nitroarenes into anilines and nitroalkanes into alkylhydroxylamines by the ammonia× borane complex. No dehalohalogenation was seen in the case of chloro- or bromonitroarenes, while ester, cyano, or carboxylic acid functionalities also remain intact. The nitroarene to aniline reduction pathway does not require nitrosoarenes as intermediate products. Copyright
