STEREOCHEMISTRY OF ORGANIC SULPHUR COMPOUNDS. Part 13. CONFIGURATIONAL ASSIGNMENT OF DIASTEREOISOMERS OF 2-METHYLSULPHINYL-1,2-DIPHENYLETHANOL AND THEIR O-METHYL AND O-ACETYL DERIVATIVES

Article abstract of DOI:10.1016/S0040-4020(01)88442-8

The synthesis, isolation and conformational analysis of the diastereomeric 2-methylsulphinyl-1,2-diphenylethanol and its O-methyl and O-acetyl derivatives are reported.Chemical correlations and the study of the influence of solvent polarity changes on the coupling constants have permitted the configurational assignment.Lanthanide shift reagents have been used also to this effect.The role of hydrogen bonding in the hydroxysulphoxides has been evaluated in diluted solutions by IR and NMR spectroscopy.A donor-acceptor interaction between oxygen and sulphur has been invoked to explain the differences in conformational behaviuor between epimeric sulphoxides at sulphur atom.