Abstract
2-Iodobenzothiazole was reacted with tributyl(trifluorovinyl)tin and (2-chlorodifluorovinyl)tributyltin by the Stille reaction to yield 2-trifluorovinyl- and 2-(2-chlorodifluorovinyl)benzothiazole, respectively. The quaternary salt of 2-trifluorovinylbenzothiazole, when treated with fluoride ion, furnished the corresponding thiacarbocyanine dye containing a perfluorinated polymethine chain. The reaction involved nontrivial cleavage of the C–C bond to provide an energetically advantageous conjugated perfluoropolyenic system.
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