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ORIGINAL RESEARCH article

Front. Chem.

Sec. Organic Chemistry

Volume 13 - 2025 | doi: 10.3389/fchem.2025.1666772

This article is part of the Research TopicExploring Novel Pathways and Applications in Heterocyclic ChemistryView all articles

Formal synthesis of dibenzotetrathiafulvalene (DBTTF), through practical electrochemical preparation of benzo[d]-1,3-dithiole-2-one (BDTO)

Provisionally accepted
Álvaro V Terán-AlcocerÁlvaro V Terán-Alcocer1Fernanda M J Cifuentes-AjuchanFernanda M J Cifuentes-Ajuchan2Byron J López-MayorgaByron J López-Mayorga2Bernardo Antonio Frontana-UribeBernardo Antonio Frontana-Uribe1*
  • 1National Autonomous University of Mexico, México City, Mexico
  • 2Universidad de San Carlos de Guatemala, Guatemala City, Guatemala

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This study focuses on developing an electrochemical reaction to produce benzo[d]-1,3-dithiole-2-one (BDTO). This compound serves as a direct precursor for dibenzotetrathiafulvalenes (DBTTF), an important member of the charge transfer complex family. BDTO is synthesized in three steps (16%) starting from aniline. The key reaction is an anodically driven intramolecular cyclization (35%), involving a thiyl radical-cation intermediate formed from the oxidation of the S-aryl-O-ethyldithiocarbonate derivative. This derivative is obtained in good yields from its respective aromatic diazonium salt. This approach eliminates the need for advanced, costly intermediates and avoids long, complex synthetic routes previously used to produce BDTO, utilizing safer and cheaper reagents. This opens the door to generating DBTTF derivatives quickly.

Keywords: DBTTF, benzo[d]-1,3-dithiole-2-ones (BDTO), Electrosynthesis, Electrochemical cyclization, O-ethyl-S-phenyldithiocarbonate

Received: 15 Jul 2025; Accepted: 18 Aug 2025.

Copyright: © 2025 Terán-Alcocer, Cifuentes-Ajuchan, López-Mayorga and Frontana-Uribe. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

* Correspondence: Bernardo Antonio Frontana-Uribe, National Autonomous University of Mexico, México City, Mexico

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Supplementary Material