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

✍ Scribed by Grzegorz Mlostoń; Marta Woźnicka; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
78 KB
Volume
90
Category
Article
ISSN
0018-019X

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✦ Synopsis

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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