Synthesis of a chiral monosubstituted derivative of bis(ethylenedithio)tetrathiafulvalene: reaction of the cyclic sulfate ester of R,R-1,4-difluorobutane-2,3-diol with 2-thioxo-1,3-dithiole-4,5-dithiolate

Abstract

2-Thioxo-1,3-dithiole-4,5-dithiolate reacts stereospecifically with the cyclic sulfate ester of R,R-1,4-difluorobutane-2,3-diol by two nucleophilic attacks, ring opening of the cyclic sulfate ester at carbon and displacement of the nearer fluorine atom, to form a derivative of the 1,3-dithiolo[4,5-b]-1,4-dithiin ring system. This product is converted in two steps into an analogue of bis(ethylenedithio)tetrathiafulvalene with a 2-fluoro-1-hydroxyethyl side-chain, a new substrate for the preparation of electroactive materials.