Studies of the regioselective ring-opening–closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives |
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| Authors: | Aleksandar Rašović Andreas Koch Erich Kleinpeter Rade Marković |
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| Institution: | 1. Center for Chemistry ICTM, University of Belgrade, PO Box 473, 11000 Belgrade, Serbia;2. Universität Potsdam, Chemisches Institut, Karl-Liebknecht-Str. 24-25, D-14476 Potsdam (Golm), Germany;3. Faculty of Chemistry, University of Belgrade, Studentski trg 16, PO Box 158, 11001 Belgrade, Serbia |
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| Abstract: | Trithiaazapentalene derivatives were prepared by the reaction of 2-alkylidene-4-oxothiazolidines with Lawesson's reagent. They are classified as two structurally different trithiaazapentalene compounds that have different contributions of monocyclic 1,2-dithiole and 1,2,4-dithiazole structures and degrees of aromaticity of the bicyclic trithiaazapentalene system. The electron-donating ability of substituents at the C(5) position of the trithiaazapentalene system is recognized as the main cause for changes in π-electron distribution. This is the first complete study of substituent effects on the structure of trithiapentalenes. |
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| Keywords: | Trithiapentalene 1 2-Dithiole 1 2 4-Dithiazole 4-Oxothiazolidine Rearrangement to trithiaazapentalene Push&ndash pull character |
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