Syntheses of enantiopure organosulfur donors by three different strategies requiring only four-six steps are reported. The key step involves either double substitution of an enantiopure cyclic sulfate ester by a dithiolate, attachment of a chiral diol as a ketal, or completely diastereoselective cycloaddition of 1,3-dithiole-2,4,5-trithione to an enantiopure alkene.
,2R,5R,2,5, gave two separable diastereomeric thiones, which can be transformed to enantiomeric BEDT-TTF derivatives with four or eight hydroxyl groups.
Short synthetic approaches to a range of monosubstituted BEDT-TTF derivatives are described, via either cycloaddition reactions of 1,3-dithiole-2,4,5-trithione or nucleophilic substitutions of 2-thioxo-1,3-dithiole-4,5-dithiolate, followed by reaction with mercuric acetate and then coupling in the presence of triethyl phosphite. BEDT-TTF derivatives with hydroxy-and amino-functionalised side chains have been prepared with the functional group protected. Deprotection and further reactions opens up potential for attachment to groups bringing additional bulk properties, e.g. groups such as pyridine and 2,2'-bipyridine for binding magnetic metal ions, and electropolymerisable groups such as thiophenes and pyrroles. Preparation of BEDT-TTF's carrying carbonyl functionalities are also described. Strategies for preparing polysubstituted donors are discussed.
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