TADDOLs and methylcyclohexanones: selectivity, resolution and the kinetics of decomposition

Abstract

Three chiral TADDOL (α,α,α,α′-tetraaryl-2,2-disubstituted 1,3-dioxolane-4,5-dimethanol) host molecules were employed to yield inclusion compounds with three isomers of methylcyclohexanones as guests. Although 4-methylcyclohexanone was not a chiral compound due to its internal symmetry, the other two isomers were racemates, and TADDOLs acted as potential resolving agents. The selectivity preference of the methylcyclohexanones for each host was established using solution nuclear magnetic resonance (NMR) spectroscopy, and the crystal structure of each host–guest compound was elucidated by single-crystal X-ray diffraction. The packing of the structures was analysed to explain the resulting resolution of the enantiomeric guests. The kinetics of decomposition were investigated for a representative TADDOL host.