N2 - This chapter discusses the application of ionic liquids as solvent systems for the electrochemical study and electrosynthesis of organic molecules, highlighting some particular examples, with the aim to compare any similarities and differences observed in ionic liquids to behavior observed in conventional solvents. The effect of cosolvents on redox mechanisms and efficiency is discussed. Examples of electrochemical studies related to the oxidation of aromatic rings, amines, and sulfur-containing compounds, as well as the reduction of conjugated alkenes, haloalkanes, aromatic rings, and carbonyl- and nitro-containing compounds are discussed.
AB - This chapter discusses the application of ionic liquids as solvent systems for the electrochemical study and electrosynthesis of organic molecules, highlighting some particular examples, with the aim to compare any similarities and differences observed in ionic liquids to behavior observed in conventional solvents. Reactor performance increases under modulated potential or current control possibly may be significant enough to make an electrochemical processing route economically viable. User Name Password Sign In.
Fedkiw 1 and William D. Scott Jr.
This Article doi: Services Email this article to a colleague Alert me when this article is cited Alert me if a correction is posted Article Usage Statistics Similar articles in this journal Similar articles in Web of Science Add to My File Cabinet Download to citation manager Purchase a print copy of this issue Permission requests. The reaction occurred stereoselectively with no trace of cis -alkene isomer.
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Scheme 4: Putative reaction mechanism of the electrochemical Corey—Winter reaction. The potentiostatic and galvanostatic experiments were carried out in a H-cell divided cell with 25 mL of electrolytic media per compartment. Therefore, this electrochemical reaction represents a promising way to produce trans -olefins from their respective thiocarbonates, overcoming thus the toxicity and safety issues of the classical Corey—Winter reaction.
Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis
Under PCE feasibility and affordability of the reaction are limited by the potentiostat, because this device is rarely available in an organic chemistry laboratory and it can be expensive to acquire it. In the other hand, current controlled electrolysis CCE , where the electrode potential control is made indirectly by the experimental conditions, requires an ordinary and easy available direct current power source, therefore, reduction of compound 4 was attempted under CCE conditions.
This is due to the lack of potential control and when the concentration of the starting material decreases the electrode potential shifts to more negative values. When higher current density values for the electrolysis were used, TLC showed the formation of several byproducts. This indicates that the second reduction peak observed in cyclic voltammetry associated with the unsaturated ester function was reached. There are several aspects of the reaction that are currently under study to generate a robust and general olefination electrochemical method via the thiocarbonate reduction; nevertheless, this letter shows for the first time the potential use of electrochemistry with this functional group using green reduction conditions.
Application of this methodology to the synthesis of other biologically important products, the study of the reaction scope because other thiocarbonate derivatives seem to be not very reactive, as well as mechanistic details are under investigation and will be reported soon.
A new approach to convert thiocarbonates derived from 1,2-diols containing the 6-pentyl-2 H -pyranone framework to trans -alkenes by means of electrochemical reduction in an H-type separated cell was developed.
This new environmentally friendly process was used to synthetize a metabolite isolated from Trichoderma viride in high yield. The reaction can be driven by both, controlled potential and constant current electrolysis with excellent results, which is convenient for application in organic chemistry laboratories. Siegfried R.
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