Synthesis of a new polyfluorinated vinylogue of tetrathiafulvalene through 1,3-dipolar cycloaddition of ethyl beta-bromoperfluorodithiocrotonate with dimethyl acetylenedicarboxylate |
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Authors: | Timoshenko Vadim M Bouillon Jean-Philippe Chernega Alexander N Shermolovich Yuriy G Portella Charles |
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Institution: | Laboratoire Réactions Sélectives et Application, Associé au CNRS (UMR 6519), Faculté des Sciences, Université de Reims, B. P. 1039, 51687 Reims Cedex 2, France. |
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Abstract: | The ethyl ester of beta-bromoperfluorodithiocrotonic acid reacts with dimethyl acetylenedicarboxylate to give 1,4-difluoro-2,3-bis(trifluoromethyl)-but-2-ene-1,4-diylidene-2,2'-bis(4',5'-dicarbomethoxy-1',3'-dithiole) (4), a new type of vinylogue of tetrathiafulvalene. The thermal transformations of this compound lead, depending on the temperature, to the formation of the cyclization products: 11,14-difluoro-2,3,8,9-tetra(carbomethoxy)-12,13-bis(trifluoromethyl)-1,4,7,10-tetrathiadispiro4.0.4.4]tetradeca-2,8,11,13-tetraene (8) or 5,8-difluoro-6,7-bis(trifluoromethyl)-2,3-bis(carboxymethyl)-1,4-benzodithiine (11). |
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Keywords: | alkynes cycloaddition dithiocrotonic acid sulfur heterocycles tetrathiafulvalene |
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