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5-Morpholino-1,2,3,4-thiatriazole as a Sulfur-Transfer reagent in the reactions with Thioketones


Mloston, G; Woznicka, M; Heimgartner, H (2007). 5-Morpholino-1,2,3,4-thiatriazole as a Sulfur-Transfer reagent in the reactions with Thioketones. Helvetica Chimica Acta, 90(3):594-600.

Abstract

The thermal decomposition of 5-morpholino-1,2,3,4-thiatriazole (7), which leads to the extrusion of an active form of sulfur, in the presence of different thioketones is described. The interception of the S-atom by the C=S bond leads to in situ formation of an elusive thiocarbonyl S-sulfide of type 5. This
intermediate is a prone 1,3-dipole, which undergoes effectively [2+3] cycloadditions with thioketones to yield 1,2,4-trithiolane derivatives in a regioselective manner. Unexpectedly, 3,3-dichloro-2,2,4,4-tetramethyl-3-thioxocyclobutanone (1c) does not lead to the expected symmetrical 1,2,4-trithiolane. This result can be explained by the reduced stability of the corresponding thiosulfine 5c. Three-component reactions, which were carried out in the presence of equimolar amounts of two different thioketones, result in the formation of 'mixed' 1,2,4-trithiolanes of type 8.

Abstract

The thermal decomposition of 5-morpholino-1,2,3,4-thiatriazole (7), which leads to the extrusion of an active form of sulfur, in the presence of different thioketones is described. The interception of the S-atom by the C=S bond leads to in situ formation of an elusive thiocarbonyl S-sulfide of type 5. This
intermediate is a prone 1,3-dipole, which undergoes effectively [2+3] cycloadditions with thioketones to yield 1,2,4-trithiolane derivatives in a regioselective manner. Unexpectedly, 3,3-dichloro-2,2,4,4-tetramethyl-3-thioxocyclobutanone (1c) does not lead to the expected symmetrical 1,2,4-trithiolane. This result can be explained by the reduced stability of the corresponding thiosulfine 5c. Three-component reactions, which were carried out in the presence of equimolar amounts of two different thioketones, result in the formation of 'mixed' 1,2,4-trithiolanes of type 8.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2007
Deposited On:08 Nov 2011 10:14
Last Modified:07 Dec 2017 09:31
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Polish State Committee for Scientific Research (grant 4T09A04625)), F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200790060

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