99843-65-9Relevant academic research and scientific papers
Electrochemical reactivity of S-phenacyl-O-ethyl-xanthates in hydroalcoholic (MeOH/H2O 4:1) and anhydrous acetonitrile media
López-López, Ernesto Emmanuel,López-Jiménez, Sergio J.,Barroso-Flores, Joaquín,Rodríguez-Cárdenas, Esdrey,Tapia-Tapia, Melina,López-Téllez, Gustavo,Miranda, Luis D.,Frontana-Uribe, Bernardo A.
, (2021)
The electrochemical behavior of a series of S-phenacyl-O-ethyl-xanthates (O-ethyl-dithiocarbonate acetophenone derivatives) in hydroalcoholic (MeOH/H2O 4:1) and anhydrous media (ACN/TBAPF6) using carbon electrodes was studied. Cyclic voltammetry showed in hydroalcoholic media only two cathodic waves, whereas in ACN one anodic and two cathodic waves were present. The first cathodic wave corresponded to the reduction of the phenylketone group, whereas the first anodic was attributed to the xanthate unit. Macroelectrolysis on graphite and vitreous carbon at anodic and cathodic potentials, let us to explore the synthetic potential of this electrochemical reactions. With some compounds in hydroalcoholic media and using carbon electrodes, polymeric material was deposited on the electrode impeding the reaction; this deposit was characterized by AFM and SEM-EDS. The electroreduction on Ti electrode overcome this problem and gave the corresponding acetophenones (>95%). On the other hand, in ACN, small quantities of the dimeric 1,4-dicarbonyl compounds X-PhCOCH2CH2COPh-X (7–15%), as well as the corresponding acetophenones (ca. 50%) were isolated. Oxidation macroelectrolysis showed a very complicated transformation without synthetic value. The reaction mechanism for the reduction and the homolytic dissociation into the phenacyl radical was supported by DFT calculations.
A simple method for the synthesis of furfuryl ketones and furylacetic acid derivatives
Chalikidi, Petrakis N.,Nevolina, Tatyana A.,Uchuskin, Maxim G.,Abaev, Vladimir T.,Butin, Alexander V.
, p. 621 - 629 (2015/10/12)
A simple preparative method has been developed for the synthesis of aryl(furfuryl) ketones, amides, and furylacetic acid esters, based on radical alkylation of furan derivatives at the α-position with O-ethyl(phenacyl)xanthogenates and phenacyl iodides in the presence of Fenton's reagent (H2O2/FeSO4·7H2O) in DMSO. The range of applicability and mechanisms for the formation of major and side products have been considered.
