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 OpenAlex

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

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DB	Citing
Web of science	1

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