61836-77-9Relevant academic research and scientific papers
Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses
Liang, Fengying,Eda, Kazuo,Okazoe, Takashi,Wada, Akihiro,Mori, Nobuaki,Konishi, Katsuhiko,Tsuda, Akihiko
, p. 6504 - 6517 (2021/05/06)
The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.
One-Pot Conversion of Primary Alkyl Chlorides and Dichlorides into Alcohols, Diols, and Ethers via Formic Ester Intermediates under Phase-Transfer Conditions
Zahalka, Hayder A.,Sasson, Yoel
, p. 763 - 765 (2007/10/02)
A procedure for the synthesis of alkyl formates, 1,ω-alkanediyl diformates, and unsaturated analogs from alkyl (or 2-alkenyl) halides and sodium formate under solid/liquid phase-transfer conditions is reported.For conversion into alcohols or diols, respectively, the formic esters can be directly hydrolyzed in the reaction mixture of their preparation.Using a related procedure, cyclic ethers are prepared from 1,ω-dichloroalkanes, sodium formate, and potassium hydroxide under solid/liquid phase-transfer conditions.
