Electrochemical Reduction of 1H-Thioxanthene-1,4,9-trione and 3-Methyl-1H-thioxanthene-1,4,9-trione Representatives of a New Class of Heterocycles Related to Thioxanthenone Full article
Journal |
European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690 |
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Output data | Year: 2023, Volume: 26, Number: 33, Pages: 1 Pages count : 1 DOI: 10.1002/ejoc.202300459 | ||
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Funding (1)
1 | Российский Научный Фонд | 22-13-00108 |
Abstract:
A convenientsyntheticroutewas proposedfor the synthesisof3-methyl-1H-thioxanthene-1,4,9-trione.This compoundand its3-H congenerare representativesof a newclassof thioxan-thone-likeheterocycles,whichcan be usedas buildingblocksfor materialsusedin organicelectronics.Electrochemicalreduction(ECR)of 1H-thioxanthene-1,4,9-trioneand its 3-methylderivativein DMFand acetonitrileis a three-stageprocessleadingto the formationof the correspondinglong-livedradicalanionsand unstabledianionsat the first and secondstages,respectively.In a protolyticequilibrium,dianionsare convertedinto 1-oxy-4-hydroxy-1H-thioxanthene-9-oneanions.Theirone-electronreversibleECR leadsto the correspondingradicaldianions,followedby the formationof (3-methyl/H)-1,4-dihy-droxy-1H-thioxantene-9-onesas the finalproducts.The lattercompoundscan be convertedinto the initial(3-methyl/H)-1H-thioxanthene-1,4,9-triones.The mainintermediateswerechar-acterizedusinga combinationof cyclicvoltammetry,EPRspectroscopy,3D spectroelectrochemistry,and DFT calculationsat the (U)B3LYP/6-31+G*/PCMlevelof theory.A generalECRschemewas proposedfor both typesof compounds.
Cite:
Odintsov D.S.
, Os'kina I.A.
, Irtegova I.G.
, Shundrin L.A.
Electrochemical Reduction of 1H-Thioxanthene-1,4,9-trione and 3-Methyl-1H-thioxanthene-1,4,9-trione Representatives of a New Class of Heterocycles Related to Thioxanthenone
European Journal of Organic Chemistry. 2023. V.26. N33. P.1. DOI: 10.1002/ejoc.202300459 WOS РИНЦ
Electrochemical Reduction of 1H-Thioxanthene-1,4,9-trione and 3-Methyl-1H-thioxanthene-1,4,9-trione Representatives of a New Class of Heterocycles Related to Thioxanthenone
European Journal of Organic Chemistry. 2023. V.26. N33. P.1. DOI: 10.1002/ejoc.202300459 WOS РИНЦ
Dates:
Submitted: | May 12, 2023 |
Accepted: | Jul 5, 2023 |
Published print: | Jul 6, 2023 |
Published online: | Jul 31, 2023 |
Identifiers:
Web of science | WOS:001037557500001 |
Elibrary | 62766059 |
OpenAlex | W4383375896 |