3,4-Dichloro-1,2,5-thiadiazole: A commercially available electrophilic sulfur transfer agent and safe resource of ethanedinitrile

Gorjian, Hayedeh and Khaligh, Nader Ghaffari (2022) 3,4-Dichloro-1,2,5-thiadiazole: A commercially available electrophilic sulfur transfer agent and safe resource of ethanedinitrile. Journal of Sulfur Chemistry, 43 (2). pp. 169-179. ISSN 1741-5993, DOI https://doi.org/10.1080/17415993.2021.1991928.

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Abstract

3,4-Dichloro-1,2,5-thiadiazole is introduced as a safe and efficient sulfur transfer reagent. By applying this commercially available reagent, the symmetrical trisulfides and ethanedinitrile were simultaneously obtained by reacting various thiols with this reagent at room temperature. This reagent is non-toxic, inexpensive, and commercially available. In addition, no higher-order polysulfides were detected in all cases after the completion of the reaction. The short reaction times (20-50 min), excellent selectivity, and high yield of the trisulfides are some attractive merits of this reagent for the preparation of trisulfides. The reaction is one-pot, and isolation-purification of intermediates is not required. The procedure was readily scaled up to 5 grams. A mechanism is presented to explain the chemistry.

Item Type: Article
Funders: Universiti Malaya, Kuala Lumpur, Malaysia (Grant No: IF065-2020)
Uncontrolled Keywords: Heterocycle; Sulfur transfer reagent; Trisulfide; Ethanedinitrile; One-pot reaction
Subjects: Q Science > QD Chemistry
Divisions: Nanotechnology & Catalysis Research Centre
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 23 Oct 2023 05:56
Last Modified: 23 Oct 2023 05:56
URI: http://eprints.um.edu.my/id/eprint/41810

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