Differences In Conformational Behavior Research Articles

Stereochemistry of organic sulphur compounds. part 13. Configurational assignment of diastereoisomers of 2-methylsulphinyl-1,2-diphenylethanol and of their [formula omitted]-methyl and [formula omitted]-acetyl derivatives

The synthesis, isolation and conformational analysis of the diastereomeric 2-methylsulphinyl-1,2-diphenylethanol and of 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 behaviour between epimeric sulphoxides at sulphur atom.