Electric Literature of 21436-03-3. Let’s face it, organic chemistry can seem difficult to learn. Especially from a beginner’s point of view. Like 21436-03-3, Name is (1S,2S)-Cyclohexane-1,2-diamine. In a document type is Article, introducing its new discovery.
The chiral triplesalen ligand H6chand provides three chiral salen ligand compartments in a meta-phenylene arrangement by a phloroglucinol backbone. The two diastereomeric versions H6chand RR and H 6chand rac have been used to synthesize the enantiomerically pure chiral complex [(FeCl)3-(chand RR)] (3 RR) and the racemic complex [(FeCl)3(chand rac)] (3 rac). The molecular structure of the free ligand H6chand rac exhibits at the terminal donor sides the O-protonated phenol-imine tautomer and at the central donor sides the N-protonated keto-enamine tautomer. The trinuclear complexes are comprised of five-coordinate square-pyramidal Fe III ions with a chloride at the axial positions. The crystal structure of 3 rac exhibits collinear chiral channels of ?11 A in diameter making up 33.6 % of the volume of the crystals, whereas the crystal structure of 3 RR exhibits voids of 560 A 3. Moessbauer spectroscopy demonstrates the presence of Fe III high-spin ions. UV/Vis spectroscopy is in accordance with a large delocalized system in the central backbone evidenced by strong low-energy shifts of the imine pi-pi * transitions relative to that of the terminal units. Magnetic measurements reveal weak intramolecular exchange interactions but strong magnetic anisotropies of the Fe III ions. Complexes 3 rac and 3 RR are good catalysts for the sulfoxidation of sulfides providing very good yields and high selectivities with 3 RR being enantioselective. A comparison of 3 RR and [FeCl-(salen’)] provides higher yields and selectivities but lower enantiomeric excess values (ee values) for 3 RR relative to [FeCl(salen’)]. The low ee values of 3 RR appeared to be connected to a strong ligand folding in 3 RR, opening access to the catalytically active high-valent Fe-O species. The higher selectivity is assigned to a cooperative stabilization of the catalytically active high-valent Fe-O species through the phloroglucinol backbone in the trinuclear complexes.
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