Synthesis of Mesoionic 1,3,4-Thiadiazole-2-Thiolates

A reliable synthesis of C5-unsubstituted 1,3,4-thiadiazole-2-thiolates is described that avoids potentially explosive or laborious steps. This work presents a reliable method for preparing the starting material dithioformate from carbon disulfide and potassium or sodium tri-sec-butylhydroborates for the preparation of the mesoionic title compounds with potassium hydrazinecarbodithioates. New 1,3,4-thiadiazole-2-thiolates are presented, and missing structural analysis data of known derivatives are added (1D- and 2D-NMR, HR-ESI-MS, IR).

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Publication Details

Journal
Molbank
Published
2025-05-22
DOI
https://doi.org/10.3390/m2010
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Synthesis of Mesoionic 1,3,4-Thiadiazole-2-Thiolates

Andreas Schmidt, Sean Ray Kahnert
Molbank
Sulfur-Based Synthesis Techniques
article

Synthesis of Mesoionic 1,3,4-Thiadiazole-2-Thiolates

Andreas Schmidt, Sean Ray Kahnert
article en

Abstract

A reliable synthesis of C5-unsubstituted 1,3,4-thiadiazole-2-thiolates is described that avoids potentially explosive or laborious steps. This work presents a reliable method for preparing the starting material dithioformate from carbon disulfide and potassium or sodium tri-sec-butylhydroborates for the preparation of the mesoionic title compounds with potassium hydrazinecarbodithioates. New 1,3,4-thiadiazole-2-thiolates are presented, and missing structural analysis data of known derivatives are added (1D- and 2D-NMR, HR-ESI-MS, IR).

MolbankVol. 2025(2)
Clausthal University of Technology (DE)
Openalex Percentile: Top 91%
Sulfur-Based Synthesis Techniques
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