Abstract
The chapter discusses the efforts concerning six-membered heterocycles. The relative kinetic acidity of the diastereotopic vicinal hydrogens and the thermodynamic nonequivalence of the α-metallated species in the lithiation-alkylation reaction of organic sulfoxides depend upon the orientation of the sulfinyl group. The chapter discusses the conformational equilibria of thiane-1-oxide, conformational analysis of oxidative S-oxides, 5-sulfinyl-1,3-dioxanes, and of 2-oxo-1,3,2- dioxathianes. Much of the sustained interest in the conformational analysis of sulfoxides was initiated by the discovery of the axial preference of the sulfinyl oxygen in thiane-1-oxide. The molecular structure of thiane-1-oxide has been determined by gas-phase electron diffraction. The collected data indicate that the molecule adopts a chair conformation with an axial orientation of the oxygen atom, and there is no indication of any appreciable amount of equatorial form.
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