Spontaneous Resolution of the Fe(CO) Anion and Inclusion of Chiral Guest Molecules in BEDT-TTF Radical-Cation Salts.

We report the synthesis of three radical-cation salts of BEDT-TTF from racemic tris(oxalato)ferrate by electrocrystallization in the presence of chiral molecules. In the presence of enantiopure l-(+)-tartaric acid, we observe spontaneous resolution of the labile tris(oxalato)ferrate anion to produce the chiral radical-cation salt α-(BEDT-TTF)[Δ-Fe(CO)].[l-(+)-tartaric acid] which contains only the Δ enantiomer of Fe(CO). Using enantiopure ()-(-)-3-hydroxytetrahydrofuran as an additive gives α-(BEDT-TTF)[Fe(oxalate)].(HO).ethanol.()-(-)-3-hydroxytetrahydrofuran, which includes the chiral guest and contains a racemic mixture of Λ and Δ enantiomers of Fe(CO). Enantiopure ()-phenyloxirane is hydrolyzed to racemic 1-phenylethane-1,2-diol to produce racemic β"-β"-(BEDT-TTF)(HO/HO)Fe(CO).1-phenylethane-1,2-diol.