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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.

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Metadaten
Author:Aleksandar Rasovic, Andreas Koch, Erich Kleinpeter, Rade Markovic
DOI:https://doi.org/10.1016/j.tet.2013.10.088
ISSN:0040-4020 (print)
Parent Title (English):Tetrahedron
Publisher:Elsevier
Place of publication:Oxford
Document Type:Article
Language:English
Year of first Publication:2013
Year of Completion: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
Pagenumber:9
First Page:10849
Last Page:10857
Funder: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