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5‐Morpholino‐1,2,3,4‐thiatriazole as a Sulfur‐Transfer Reagent in the Reactions with Thioketones
Author(s) -
Mlostoń Grzegorz,
Woźnicka Marta,
Heimgartner Heinz
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790060
Subject(s) - chemistry , reagent , sulfur , yield (engineering) , sulfide , regioselectivity , decomposition , thermal decomposition , morpholino , medicinal chemistry , organic chemistry , catalysis , thermodynamics , biochemistry , zebrafish , gene , physics
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 CS 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 .