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Synthesis of hetaryl-substituted 1,2,4-trithiolanes via a three-component reaction with dihetaryl thioketones, benzyl azide, and 2,2,4,4-tetramethyl-3-thioxocyclobutanone


Mlostoń, Grzegorz; Celeda, Malgorzata; Linden, Anthony; Heimgartner, Heinz (2016). Synthesis of hetaryl-substituted 1,2,4-trithiolanes via a three-component reaction with dihetaryl thioketones, benzyl azide, and 2,2,4,4-tetramethyl-3-thioxocyclobutanone. Journal of Sulfur Chemistry, 37(1):14-22.

Abstract

The three-component reactions with a hetaryl thioketone, 2,2,4,4-tetramethyl-3-thioxocyclobutanone, and excess benzyl azide performed at 60°C in the presence of LiClO4 lead to the formation of two types of 1,2,4-trithiolanes. As the major products, the non-symmetrical dihetaryl-substituted spiro-1,2,4- trithiolanes are formed. In addition, the symmetrical dispiro-1,2,4-trithiolane is identified. These products are formed in competitive [3 + 2] cycloadditions of the in-situ-generated thiocarbonyl S-sulfide with the thioketones used in the reaction.

Abstract

The three-component reactions with a hetaryl thioketone, 2,2,4,4-tetramethyl-3-thioxocyclobutanone, and excess benzyl azide performed at 60°C in the presence of LiClO4 lead to the formation of two types of 1,2,4-trithiolanes. As the major products, the non-symmetrical dihetaryl-substituted spiro-1,2,4- trithiolanes are formed. In addition, the symmetrical dispiro-1,2,4-trithiolane is identified. These products are formed in competitive [3 + 2] cycloadditions of the in-situ-generated thiocarbonyl S-sulfide with the thioketones used in the reaction.

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > General Chemistry
Language:English
Date:February 2016
Deposited On:15 Oct 2015 14:37
Last Modified:26 Jan 2022 06:46
Publisher:Taylor & Francis
ISSN:1741-5993
Funders:National Science Center (Cracow, Poland)
Additional Information:This is an Accepted Manuscript of an article published by Taylor & Francis in Journal of Sulfur Chemistry on September 12, 2015, available online: http://wwww.tandfonline.com/10.1080/17415993.2015.1082182
OA Status:Green
Publisher DOI:https://doi.org/10.1080/17415993.2015.1082182