91667-26-4Relevant academic research and scientific papers
Synthesis of (: Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid
Da Silva, Vitor A. F.,Da Silva, Gustavo P.,Matsuo, Bianca T.,Ali, Akbar,Davis, Rebecca L.,Zukerman-Schpector, Julio,Corrêa, Arlene G.,Paix?o, Márcio W.
, p. 519 - 526 (2019/01/24)
A convenient and broadly applicable method for the hydrohalogenation of ynones is described, by the combination of halotrimethylsilanes and tetrafluoroboric acid. Practically, one equivalent of HX (Br?nsted acid) and BF3 (Lewis acid) is smoothly generated, which activates the carbonyl compounds. Through this protocol, 42 examples of (Z)-β-halovinyl carbonyl compounds (Cl, Br and I) were obtained, in good yields and high stereoselectivity having 2-MeTHF as a solvent.
Metal-free, Regio-, and Stereo-Controlled Hydrochlorination and Hydrobromination of Ynones and Ynamides
Zeng, Xiaojun,Lu, Zhichao,Liu, Shiwen,Hammond, Gerald B.,Xu, Bo
, p. 13179 - 13187 (2017/12/26)
We developed an atom-economical and metal-free method for the regio- and stereo-selective hydrohalogenation of ynones and ynamides using easy to handle DMPU/HX (X = Br or Cl) reagents. The reaction operates under mild conditions and a range of functional groups is well tolerated. We propose that the hydrohalogenation of ynones gives the anti-addition products via a concerted multimolecular AdE3 mechanism and that the hydrohalogenation of ynamides produces the syn-addition products via a cationic keteniminium intermediate.
Regioselective synthesis of (trifluoromethyl)-β-chloroenones
Alvernhe, Gerard,Bensadat, Abdelkader,Ghobsi, Abdelkader,Laurent, Andre,Laurent, Eliane
, p. 169 - 172 (2007/10/03)
The regioselectivity of the conversion of 1,3-diketones into β-chloroenones can be changed by the appropriate choice of the reagent: reaction with "Vilsmeier's reagent" prepared from POCl3 and dimethylformamide or treatment of the diketone with the oxalyl chloride in the presence of dimethylformamide.
