Dihydrolevoglucosenone (DLG or Cyrene™) solvent is a green dipolar solvent produced from cellulose waste. Different studies have demonstrated that it can successfully replace dipolar solvents, such as ,-dimethylformamide (DMF), ,-dimethylacetamide (DMA) and -methylpyrrolidinone (NMP), in a variety of chemical reactions. In this paper, the first application of DLG in organic electrosynthesis is described, with results of its use in the electrochemical reduction of benzophenone derivatives ( = -1.75 V Ag/AgCl), as a greener alternative to other dipolar solvents with environmental concerns. Conductivity measurements show that the solvent presents conductivity and viscosity limitations that can be overcome by using EtOH as a cosolvent. The DLG/EtOH mixture resulted in a convenient solvent to carry out galvanostatic electroreductions of starting materials that exhibit high potential value. Furthermore, the reaction pathway (1e or 2e) was found to be dependent on the supporting electrolyte used; TBABF favored 2e reduction to the corresponding alcohol (52-85%), whereas LiClO promoted C-C pinacolic coupling (47-70%).
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http://dx.doi.org/10.1039/d3fd00064h | DOI Listing |
Water Res
December 2024
Shanghai Engineering Research Center of Biotransformation of Organic Solid Waste, School of Ecological and Environmental Sciences, East China Normal University, Shanghai 200241, China.
This paper investigates the efficient degradation of ciprofloxacin (CIP) in a sustainable γ-valerolactone (GVL) and water (H₂O) mixed system by controlling proton transfer and reducing the self-decay rate of Fe(VI). The kinetic model reveals that the GVL/H₂O system exhibits a rate constant of (9.7 ± 0.
View Article and Find Full Text PDFChemSusChem
December 2024
University of Rome La Sapienza, Department of Chemistry, P.le A. Moro 5, 00185, Rome, ITALY.
This work illustrates a physico-chemical study of the structural, dynamic, and transport properties of electrolytes made of LiTFSI solutions in sulphoxide and sulphone solvent mixtures. Experimental measurements, by Raman and NMR spectroscopies, as well as electrochemical impedance spectroscopy, reveal the formation of a variety of ionic aggregates depending on the solvent composition that significantly affect the ion mobility and conductivity of the electrolyte. Mixtures containing tetrahydrothiophene-1-oxide exhibit a larger ion mobility due to a rapid exchange mechanism between solvent molecules, whereas the use of tetramethylene sulphone favors the formation of ionic aggregates due to the strong dipolar interactions between solvent molecules.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
Institute of Industrial Science, The University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan.
The chiral amine catalyzed diastereo- and enantioselective [3 + 2] cycloaddition between isatin-derived azomethine ylides and α,β-unsaturated aldehydes was successfully carried out to afford spiro[oxindole-3,2'-pyrrolidine]s. It was anticipated that the formation of azomethine ylides occurred the cycloreversion of dispirooxindole-imidazolidines, which are precursor imine homodimers, in aqueous solvents.
View Article and Find Full Text PDFRSC Adv
December 2024
Department of Materials Science, University of Milano Bicocca Via R.Cozzi 55 Milano I-20125 Italy
Micellar catalysis is becoming an increasingly versatile tool to carry out a wide range of organic transformations using water as the reaction medium. The approach was recently found to be effective also in the case of water sensitive organics such as acyl chlorides. This finding is of great relevance for the manufacturing of challenging substrates such as the known iodinated contrast agent iopamidol, requiring the use of aprotic dipolar solvents (DMF, NMP, DMAc) in the key amidation step of an acyl dichloride intermediate with serinol.
View Article and Find Full Text PDFInt J Mol Sci
November 2024
Research Institute of Chemistry, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya Street, 117198 Moscow, Russia.
Herein, we describe a novel coupling between ambiphilic 2-pyridylselenyl reagents and nitriles featuring an active α-methylene group. Depending on the solvent employed, this reaction can yield two distinct types of cationic pyridinium-fused selenium-containing heterocycles, 1,3-selenazolium or 1,2,4-selenadiazolium salts, in high yields. This is in contrast to what we observed before for other nitriles.
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