631-22-1Relevant articles and documents
Base-mediated reactions of diethyl malonates derivatives with perfluorinated olefins: Novel synthetic routes to multifunctional ionomer precursors
Hirschberg, Markus E.,Pajkert, Romana,R?schenthaler, Gerd-Volker,Tverdomed, Sergey N.
, (2021/08/19)
A novel synthetic method for the preparation of per- and polyfluorinated unsaturated 2-substituted malonates is presented involving the deprotonation of the starting diethyl malonate by a strong base, followed by in situ addition of the C-nucleophile to the terminal double bond of the perfluorinated olefin. Subsequent elimination of the corresponding leaving groups and restoring of the double bond leads to the target bifunctional perfluorinated olefins. In the case of unsubstituted diethyl malonate, the elimination is accompanied by a prototropic rearrangement with a double bond migration and the addition of a second equivalent of the C-nucleophile forming the tetrafunctional internal olefins. The reaction conditions, factors affecting the reactivity and regioselectivity of the process, the choice of reagent as well as the course of competitive reactions are also discussed.
Alkyl Halides via Visible Light Mediated Dehalogenation
Rathnayake, Manjula D.,Weaver, Jimmie D.
supporting information, p. 9681 - 9687 (2019/11/28)
Net selective bromination and chlorination of activated C-H bonds can be effected in generally high yield via a simple perhalogenation/dehalogenation sequence. The photochemical reductions require no photocatalyst, relying instead on the formation of an electron donor-acceptor complex of the substrate and reductant, or alternatively autophotocatalysis. Some reactions proceed despite any apparent photon absorption, serving as a cautionary tale for other photochemical reactions involving amines. Mechanistic experiments provide an explanation for this observation.
Solvent-Controlled α-Monobromination, α,α-Dibromination or Imidation of 1,3-Diketones with N-Bromosuccinimide
Zou, Liang-Hua,Li, Yan-Chun,Li, Ping-Gui,Zhou, Jing,Wu, Zhimeng
supporting information, p. 5639 - 5643 (2018/10/05)
In this work, we present a solvent-controlled regioselective method for α-monobromination, dibromination or imidation of 1,3-diketones with N-bromosuccinimide under simple reaction conditions. The employment of solvents plays a key role on the reaction selectivity providing α-monobrominated, dibrominated and imidated products. Visible light irradiation accelerates the dibromination reaction of 1,3-diketones. In particular, one important solvent was found to be highly effective for the imidation of 1,3-diketones under base-free condition.
