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- Title
Bildung von 1,2,4-Trithiolanen in Dreikomponenten-Gemischen aus Phenyl-azid, aromatischen Thioketonen und 2,2,4,4-Tetramethylcyclobutanthionen: Eine Schwefel-Transfer-Reaktion unter Bildung von 'Thiocarbonylthiolaten' ((Alkylidensulfonio)thiolaten) als reaktive Zwischenstufen
- Authors
Mlostoń, Grzegorz; Heimgartner, Heinz
- Abstract
Formation of 1,2,4-Trithiolanes in Three-Component Reactions of Phenyl Azide, Aromatic Thiones, and 2,2,4,4-Tetramethylcyclobutanethiones: A Sulfur-Transfer Reaction to 'Thiocarbonyl-thiolates' ((Alkylidenesulfonio)-thiolates) as Reactive Intermediates The reaction of PhN3 and aromatic thioketones 18 (two-component reaction) at 80° yields only the corresponding imines 22, S, and N2. Under similar conditions, in the presence of sterically crowded 2,2,4,4-tetramethyl-cyclobutanethiones 19 (three-component reaction), 1,2,4-trithiolanes of type 20 are formed in good yields in addition to imines 22 ( Scheme 4). In case of 19a and 19c (X = CO, CS), the symmetrical trithiolanes 21a and 21b, respectively, are also isolated. With 4,4-dimethyl-2-phenyl-1,3-thiazole-5(4 H)-thione ( 24) instead of aromatic thioketone 18, imine 25, trithiolane 21a, and 1,4,2-dithiazolidine 26 are formed ( Scheme 5). A reaction mechanism for the formation of 1,2,4-trithiolanes 20 and 21, including an S-transfer to generate 'thiocarbonyl-thiolates' 2b and/or 2c and 1,3-dipolar cycloaddition with a thioketone, is proposed in Scheme 7.
- Publication
Helvetica Chimica Acta, 1995, Vol 78, Issue 5, p1298
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19950780520