Stereochemistry of organic sulphur compounds. part 14 . synthesis and conformation analysis of 1-thioderivatives of 3,3-dimethyl-2-butanol and its acetates

Abstract

Abstract The synthesis and conformational analysis of some thioderivatives But-CHX-CH2Y (X = OH and OAc: Y = SH, SMe, SO2Me and SMe2) are reported. The conformational equilibra have been established from IH-NMR data and high dilution ir studies. All the compounds exhibited almost monoconformational behaviour around the C(1)-C(2) bond, due to strong steric factors. The observed vicinal coupling constants were used to check the different parameterizations of Altona's equation for our compounds with sulphur in distinct oxidation states. The possible dihedral angle deformations were also evaluated.