Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones - en route to the synthesis of trithiaazapentalene derivatives
- 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 pi-Celectron distribution. This is the first complete study of substituent effects on the structure of trithiapentalenes. (C) 2013 Elsevier Ltd. All rights reserved.
| Author details: | Aleksandar Rasovic, Andreas KochORCiDGND, Erich KleinpeterORCiDGND, Rade Markovic |
|---|---|
| DOI: | https://doi.org/10.1016/j.tet.2013.10.088 |
| ISSN: | 0040-4020 |
| Title of parent work (English): | Tetrahedron |
| Publisher: | Elsevier |
| Place of publishing: | Oxford |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2013 |
| Publication year: | 2013 |
| Release date: | 2017/03/26 |
| Tag: | 1,2,4-Dithiazole; 1,2-Dithiole; 4-Oxothiazolidine; Push-pull character; Rearrangement to trithiaazapentalene; Trithiapentalene |
| Volume: | 69 |
| Issue: | 51 |
| Number of pages: | 9 |
| First page: | 10849 |
| Last Page: | 10857 |
| Funding institution: | Ministry of Education, Science and Technological Development of the Republic of Serbia [172020]; Deutscher Akademischer Austauschdienst (DAAD)-project [504 252 70] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
